Standard Deduction vs. Itemizing in 2026: Which Strategy Wins Under OBBBA?

Every April, millions of Americans face a critical decision: should I take the standard deduction or itemize my deductions? This year, that decision is even more important. The OBBBA of 2025 raised the SALT (State and Local Tax) deduction cap from $10,000 to $40,400 for 2026, making itemization attractive to a broader range of high-income households. Meanwhile, the standard deduction also increased with inflation. The result: some taxpayers who previously didn't benefit from itemization now save thousands by itemizing, while others should stick with the standard deduction. Here's the complete framework to decide which strategy is right for you.

2026 Standard Deductions

First, the baseline: what is the standard deduction for 2026 (Rev. Proc. 2025-32)?

2026 Standard Deduction Amounts:

• Single: $16,100
• Married Filing Jointly (MFJ): $32,200
• Married Filing Separately (MFS): $16,100
• Head of Household (HOH): $24,150
• Qualifying Surviving Spouse: $32,200

For Taxpayers Age 65 or Older (2026) — the additional standard deduction is $2,050 for a single or head-of-household filer and $1,650 per qualifying spouse for a married couple:

• Single: $16,100 + $2,050 = $18,150
• MFJ (one spouse 65+): $32,200 + $1,650 = $33,850
• MFJ (both spouses 65+): $32,200 + $3,300 = $35,500
• HOH: $24,150 + $2,050 = $26,200

These amounts increased from 2025 due to annual inflation adjustments. The standard deduction is indexed to inflation and rises each year.

Do not forget the OBBBA senior deduction. For tax years 2025 through 2028 there is a further $6,000 per person aged 65 or older, and unlike the amounts above it is available whether you itemize or not. It phases out at 6 cents per dollar of MAGI above $75,000 single or $150,000 joint. This matters enormously to the itemize-or-not decision for retirees, because it does not sit on either side of the comparison — you get it either way, so it never tips the choice, but it does mean a 70-year-old's real deduction floor is far higher than the standard-deduction table suggests.

A structural point worth internalising before any of the arithmetic below: the standard deduction is not a target you have to beat by a lot. Itemizing $200 more than the standard deduction is worth $200 × your marginal rate — perhaps $48 — in exchange for keeping receipts all year and filing a Schedule A. The decision only becomes financially interesting when the gap is in the thousands.

What Can You Itemize?

When you itemize, you add up eligible deductions and report them on Schedule A. Here's what qualifies for 2026:

The Big Three

1. State and Local Taxes (SALT) — up to $40,400 total for 2026

   • State income tax (or sales tax instead, if that is larger — you choose one, not both)
   • Local income tax (NYC, Philadelphia, etc.)
   • Property tax on your home
   • The raised cap is OBBBA's doing and is the biggest change for 2026. It is not a flat $40,400 for everyone: it phases down by 30 cents per dollar of MAGI above $505,000, and never falls below the old $10,000 floor. A joint filer at $600,000 of MAGI therefore has a cap of $40,400 − (30% × $95,000) = $11,900, not $40,400. The whole cap structure reverts to $10,000 after 2029 unless Congress acts again.

2. Mortgage Interest — limited to interest on $750,000 of acquisition debt

   • Interest on your primary residence and one secondary residence
   • Interest on home equity loans only where the debt was used to buy, build, or substantially improve the home
   • Not deductible on home equity borrowing used for anything else
   • The $750,000 ceiling was a TCJA provision due to expire; OBBBA made it permanent. Loans taken out on or before December 15, 2017 keep the old $1,000,000 limit

3. Charitable Contributions — deductible, but with real ceilings and, from 2026, a floor

   • Cash to public charities: up to 60% of AGI. (The 100%-of-AGI allowance people remember was a temporary pandemic-era provision and expired after 2021 — do not plan around it.)
   • Long-term appreciated securities and property to public charities: 30% of AGI; gifts to most private foundations: 20%
   • Amounts over the ceiling carry forward for five years
   • Donor-advised fund contributions are deductible when you fund the DAF, not when the DAF pays the charity — which is the entire mechanism behind bunching

   New for 2026 and easy to miss: itemized charitable contributions only count above 0.5% of AGI. On $200,000 of AGI, the first $1,000 of giving is now deductible to nobody. A household giving $2,000 a year to their church has just lost half of that deduction. The floor is applied once against the year's total, which is a quiet but real argument for bunching two years of gifts into one — the floor bites once instead of twice.

   And for non-itemizers: OBBBA restored a permanent above-the-line charitable deduction of $1,000 single / $2,000 joint starting in 2026. For the first time in years, ordinary giving is worth something to a household taking the standard deduction. If your giving is under $2,000 and you were itemizing purely to capture it, stop — you can take the standard deduction and the giving deduction both.

Partially Deductible Items (Subject to Limitations)

4. Medical Expenses

   • Only expenses exceeding 7.5% of your adjusted gross income
   • Includes insurance premiums, prescriptions, doctor visits, hospital costs, dental, vision, hearing aids, etc.
   • Example: AGI $100,000 → only medical expenses over $7,500 are deductible

5. Investment Interest (Rarely Deductible)

   • Only interest on money borrowed to buy taxable investments (not retirement accounts)
   • Limited to investment income for the year
   • Usually not significant for most taxpayers

NOT Deductible

• Unreimbursed employee business expenses. TCJA suspended these in 2018 and OBBBA made the suspension permanent — this is not a 2026 change, and anyone still expecting a deduction for their home office as a W-2 employee has been out of date for eight years
• Hobby losses (never deductible)
• Personal expenses
• Federal income tax
• Self-employment tax (though half of it is deductible above the line)
• Alimony under a divorce or separation instrument executed after 2018

One More OBBBA Limit, for the Top Bracket Only

From 2026, the value of itemized deductions is capped at 35 cents on the dollar for taxpayers whose income reaches the 37% bracket — the deduction is reduced by 2/37ths of the amount that would otherwise sit in that top band. A filer in the 37% bracket therefore gets 94.6% of the benefit they used to. It changes nothing for anyone below roughly $640,600 single or $768,700 joint of taxable income, but it does mean that "itemize $100,000 and save $37,000" is no longer true at the very top.

The Decision Tree: Should You Itemize?

Here's the simple rule:

Itemize if: your total itemized deductions exceed your standard deduction Take the standard deduction if: they don't

For example:

• Single filer, 2026 standard deduction: $16,100
• SALT + mortgage interest + charitable giving = $22,000
• Itemize: $22,000 beats $16,100 — and the benefit is the $5,900 difference, not the $22,000

But if:

• SALT + mortgage interest + charitable giving = $12,000
• Take the standard deduction: $16,100 beats $12,000

The number that actually matters is the second one: the gap, multiplied by your marginal rate. In the example above, $5,900 at a 22% marginal rate is $1,298 of tax. That is what itemizing is worth — not $22,000, and not $4,840 (22% of $22,000), which is the mistake almost everyone makes when they first run this. Since the whole calculation turns on which band your last dollars fall in, find your real marginal rate first; nothing below is meaningful without it.

Real-World Scenarios: Five Household Examples

Let's walk through five different households to see who benefits from itemization in 2026.

Scenario 1: High-Income New York City Homeowner (MFJ)

Profile:

• Married filing jointly, NYC resident
• Combined income: $400,000
• Home value: $1,500,000 (mortgage balance: $750,000)
• Annual mortgage interest: $30,000
• NYC real estate tax: $25,000
• NY state income tax: $22,000
• Charitable giving: $15,000

Deduction Calculation:

• SALT deduction: $25,000 (property tax) + $22,000 (state income tax) = $47,000 → capped at $40,400 (MAGI of $400,000 is below the $505,000 phase-down threshold, so the full cap applies)
• Mortgage interest: $30,000
• Charitable giving: $15,000, less the new 0.5%-of-AGI floor ($2,000) = $13,000
• Total itemized deductions: $83,400
• Standard deduction: $32,200
• Decision: Itemize
• Benefit: $51,200 of additional deductions — but at 24%, not 35%. Taxable income falls from $367,800 to $316,600, and the whole of that move sits inside the 24% band, which for a joint filer runs from $211,400 to $403,550 in 2026. Actual tax saving: $12,288

That last line is the single most common error in this entire subject. A $400,000 household is not "in the 35% bracket" — the 35% band does not begin until $768,700 of taxable income for joint filers. Deductions are worth the rate on the last dollars they remove, and those dollars sit at the bottom of your bracket stack.

Scenario 2: Middle-Income Texas Homeowner (MFJ)

Profile:

• Married filing jointly, Texas resident (no state income tax)
• Combined income: $180,000
• Home value: $600,000 (mortgage balance: $400,000)
• Annual mortgage interest: $15,000
• Property tax (TX): $8,000
• Charitable giving: $4,000

Deduction Calculation:

• SALT deduction: $8,000 (property tax; Texas has no state income tax, though this household could instead deduct estimated state sales tax, which on $180,000 of income is unlikely to reach $8,000 on its own but is worth checking on the IRS sales tax tables)
• Mortgage interest: $15,000
• Charitable giving: $4,000, less the 0.5%-of-AGI floor ($900) = $3,100
• Total itemized deductions: $26,100
• Standard deduction: $32,200
• Decision: Take the standard deduction — and separately claim the $2,000 above-the-line charitable deduction for joint non-itemizers, which they could not have had before 2026
• The $32,200 standard deduction exceeds the $26,100 itemized total by $6,100. Note the direction of travel: the standard deduction rose more this year than their deductions did, so a household that was borderline in 2025 may have fallen out of itemizing without changing anything

Scenario 3: High-Earning Connecticut Business Owner (Single)

Profile:

• Single, Connecticut resident
• Income: $250,000
• Home value: $1,200,000 (mortgage balance: $600,000)
• Annual mortgage interest: $18,000
• Connecticut property tax: $18,000
• Connecticut state income tax: $15,000
• Charitable giving: $8,000

Deduction Calculation:

• SALT deduction: $18,000 + $15,000 = $33,000 (below the $40,400 cap, fully deductible)
• Mortgage interest: $18,000
• Charitable giving: $8,000, less the 0.5%-of-AGI floor ($1,250) = $6,750
• Total itemized deductions: $57,750
• Standard deduction: $16,100
• Decision: Itemize
• Benefit: $41,650 of additional deductions, saving $12,566

This one straddles two bands, which is why it is worth walking through. Without itemizing, taxable income is $233,900 — inside the 32% band, which starts at $201,775 for a single filer. Itemizing drops taxable income to $192,250. So the first $32,125 of the extra deduction comes off at 32% ($10,280) and the remaining $9,525 comes off at 24% ($2,286). Total: $12,566, an effective rate of 30.2% on the deduction rather than the flat 32% the headline bracket implies.

Scenario 4: Retired Homeowner Filing as Head of Household, Age 70

Profile:

• Head of household, age 70, supporting a dependent parent
• Income: $100,000
• Home value: $400,000 (paid off, no mortgage)
• Property tax: $6,000
• State income tax: $3,000
• Charitable giving: $5,000
• Medical expenses: $12,000 (deductible only above 7.5% of $100K = $7,500)

Deduction Calculation:

• SALT deduction: $6,000 + $3,000 = $9,000
• Mortgage interest: $0 (home paid off)
• Charitable giving: $5,000, less the 0.5%-of-AGI floor ($500) = $4,500
• Medical expenses over 7.5% of AGI: $12,000 − $7,500 = $4,500
• Total itemized deductions: $18,000
• Standard deduction, HOH aged 65+: $24,150 + $2,050 = $26,200
• Decision: Take the standard deduction, by a margin of $8,200

Even with $12,000 of medical bills, the senior standard deduction wins comfortably — which is the usual result and the reason so little medical spending ever produces a deduction.

Then add the piece the comparison hides. On top of whichever deduction they take, this filer also gets OBBBA's senior deduction: $6,000, reduced by 6% of the $25,000 by which their MAGI exceeds $75,000, so $6,000 − $1,500 = $4,500. That brings their total deduction to $30,700 and it is available on both sides of the itemize/standard choice, so it never tips the decision — but a retiree who has only ever seen the old standard-deduction tables will substantially underestimate their real deduction, and therefore over-withhold. If that describes you, re-run the estimate for the full year before making a Roth conversion or a large IRA withdrawal, because the room below the next bracket is bigger than it looks.

Scenario 5: High-Net-Worth San Francisco Investor (MFJ)

Profile:

• Married filing jointly, San Francisco resident
• Investment income: $300,000 (capital gains, dividends)
• Home value: $2,500,000 (mortgage balance: $800,000)
• Annual mortgage interest: $23,000
• California state income tax: $35,000
• Property tax (CA): $28,000
• Charitable giving: $20,000

Deduction Calculation:

• SALT deduction: $28,000 + $35,000 = $63,000 → capped at $40,400 (MAGI of $300,000 is below the $505,000 phase-down threshold)
• Mortgage interest: $23,000
• Charitable giving: $20,000, less the 0.5%-of-AGI floor ($1,500) = $18,500
• Total itemized deductions: $81,900
• Standard deduction: $32,200
• Decision: Itemize — $49,700 of additional deductions

But the saving is $7,455, not the $19,610 that a 37%-bracket assumption would produce, and this scenario is the reason. Every dollar of this couple's income is long-term capital gains and qualified dividends, which are taxed on their own schedule: 0% up to $98,900 of taxable income for joint filers in 2026, 15% up to $613,700, 20% above that. Their taxable income after itemizing is $218,100 — squarely in the 15% capital gains band. Deductions come off the top of that stack, so $49,700 × 15% = $7,455.

Two further traps in this profile:

• The 3.8% net investment income tax does not care that they itemized. NIIT is charged on investment income above $250,000 of modified AGI, and itemized deductions do not reduce MAGI. Their NIIT bill is identical either way.
• A household living on investment income can be in a low tax band on a large income. That inverts the usual advice: an ordinary-income household at $300,000 would be in the 24% band and their deductions would be worth 60% more.

Note on the cap: even though this couple's SALT is $63,000, the $40,400 ceiling limits the deduction, costing them $22,600 of otherwise-deductible tax. That is the structural limit of OBBBA's expansion — it helps households whose SALT lands between $10,000 and $40,400, and does progressively less above that.

The SALT Cap Impact Under OBBBA

The SALT cap is critical to understand, and its shape matters more than its headline number:

Before OBBBA: the $10,000 cap meant many high earners in high-tax states couldn't deduct much of their SALT at all

Under OBBBA (2026): the cap is $40,400, so:

• New Jerseyans with $45,000 in SALT deduct $40,400, versus only $10,000 before
• Californians with $60,000 in SALT deduct $40,400, versus only $10,000 before
• Households with SALT above $40,400 still hit a ceiling, just a much higher one

The phase-down is the part nobody mentions. Above $505,000 of MAGI the cap falls by 30 cents for every dollar of income, with a hard floor at $10,000. In practice:

That creates a brutal band between roughly $505,000 and $606,000 of MAGI where an extra dollar of income costs you 30 cents of deduction on top of the tax on the dollar itself — an effective marginal rate materially above the stated 35%. If your income lands anywhere near that range, the timing of a bonus, an option exercise, or a Roth conversion is worth real money.

The cap also reverts to $10,000 after 2029 under current law. Any multi-year plan built on $40,400 should have an exit.

Bunching Strategy: Alternate-Year Itemizing

If your itemized deductions are close to the standard deduction (within $5,000-10,000), consider a bunching strategy:

Bunching only works when the un-bunched years fall below the standard deduction. If your itemized total clears the standard deduction every year anyway, bunching buys you nothing — you were already deducting every dollar. Here is a case where it does work.

A joint filer with a modest mortgage, $9,000 of SALT, and $8,000 a year of charitable giving (figures shown before the 0.5% floor, which is addressed just below):

The bunching household deducts $4,800 more across the two years for exactly the same giving — worth $1,152 at a 24% marginal rate. Notice what made it work: giving evenly, their itemized total never reached $32,200, so all $16,000 of charity was doing nothing. Bunching lifted one year above the line.

The 2026 charitable floor sharpens this further. Since only giving above 0.5% of AGI counts, spreading $8,000 across two years means the floor bites twice; bunching means it bites once. On $180,000 of AGI that is another $900 of deduction preserved.

Bunching Tools:

• Donor-Advised Funds (DAFs): contribute two or three years of giving in one year — deductible immediately, in full — then grant it to charities on your normal schedule over the following years. The charity's cash flow is unchanged; only the tax year of your deduction moves. This is the cleanest version of the strategy and the reason DAFs exist
• Property tax timing: paying a January instalment in December moves it into the earlier year, though the SALT cap limits how much this can achieve
• Accelerated charitable giving: pay next year's pledge in December of the current year

The catch to check first: you must be able to afford two years of giving in one calendar year. Bunching is a timing strategy, not a funding one.

The Mortgage Interest Deduction: Still Valuable in 2026

While the mortgage interest deduction has limitations, it remains one of the most valuable itemized deductions for homeowners:

2026 Mortgage Interest Deduction Limits:

• Deductible on loans up to $750,000 of acquisition debt (combined primary + secondary residence). OBBBA made this ceiling permanent; it had been scheduled to revert to $1,000,000
• Interest on home equity lines of credit (HELOCs) is deductible only if the borrowing was used to buy, build, or substantially improve the home
• Mortgages taken out on or before December 15, 2017 are grandfathered at the old $1,000,000 limit

Real Impact — and the mistake to avoid:

• Homeowner with a $500,000 mortgage at 6% pays about $30,000 of interest in year one
• At a 22% marginal rate, that year's interest is worth $6,600 — but only the portion above the standard deduction actually produces a saving, which is the point of this whole article
• Interest does not stay at $30,000. A mortgage amortises: by year 10 the same loan is throwing off roughly $25,000 of interest, by year 20 about $16,000, and by year 30 almost nothing. Multiplying the first year's saving by 30 overstates the lifetime benefit by roughly half

The honest framing is that the deduction is front-loaded and decays, and that it stops mattering entirely the year your total itemized deductions drop below the standard deduction — which for most households happens somewhere in the second decade of the loan, without any announcement. If you are weighing extra principal payments against investing, model what the payoff actually does to your interest and your timeline rather than assuming the deduction makes the mortgage cheap; for a household taking the standard deduction, the mortgage interest deduction is worth exactly zero.

For homeowners who do clear the threshold, mortgage interest combined with SALT (now up to $40,400) is usually what gets them there.

Medical Expenses: When They Help

Medical expenses only become deductible once they exceed 7.5% of your adjusted gross income. This is a high bar:

Threshold Examples:

• AGI $75,000: Medical expenses over $5,625 are deductible
• AGI $150,000: Medical expenses over $11,250 are deductible
• AGI $300,000: Medical expenses over $22,500 are deductible

Who Benefits:

• Retirees with high out-of-pocket costs (prescriptions, assisted living, private duty care)
• Families with chronic illnesses or disabilities
• People paying for long-term care or nursing facilities

For most middle-income families, medical expenses don't exceed the 7.5% threshold and thus don't help itemization.

Charitable Giving: The Most Controllable Deduction

Charitable giving is the only large itemized deduction you fully control — you cannot choose your property tax bill or your mortgage interest, but you can choose when and how you give. That makes it the lever that decides the itemize-or-not question for most borderline households.

2026 Charitable Contribution Rules:

Example:

• Income: $200,000, married filing jointly
• Annual charitable giving: $12,000, less the 0.5% floor ($1,000) = $11,000 deductible
• Combined with $25,000 SALT + $18,000 mortgage interest = $54,000 itemized
• That exceeds the $32,200 joint standard deduction by $21,800 — worth $5,232 at a 24% marginal rate

Give appreciated stock, not cash, if you hold any. Donating a share you bought for $2,000 that is now worth $10,000 gets you a $10,000 deduction and permanently erases the $8,000 of capital gain. Selling it first and donating the proceeds costs you tax on the gain and leaves you with less to give. The only requirement is that you have held it more than a year.

For households that support charities and sit near the threshold, bunching two years of giving through a Donor-Advised Fund is usually what tips itemization from marginal to clearly worthwhile.

Action Steps: Decide Your 2026 Strategy

1. Calculate your total potential itemized deductions:

   • SALT (property tax + state income or sales tax + local income tax, capped at $40,400 — less if your MAGI is above $505,000)
   • Mortgage interest (if applicable)
   • Charitable giving, counting only the amount above 0.5% of your AGI
   • Medical expenses, counting only the amount above 7.5% of your AGI

2. Compare to your 2026 standard deduction — $16,100 single, $32,200 joint, $24,150 head of household, plus $2,050 (single/HOH) or $1,650 per spouse (joint) if you are 65 or older

3. Then multiply the gap by your marginal rate. That product — not the deduction total — is what the decision is worth:

   • Itemized exceeds standard by a meaningful margin → itemize
   • Standard exceeds itemized → take the standard deduction, and remember you can still claim the $1,000/$2,000 charitable deduction and, if 65+, the $6,000 senior deduction
   • Within a thousand or so either way → the tax difference is under $250. Take the standard deduction and save yourself the recordkeeping, unless bunching can move you decisively above the line next year

4. For borderline cases: bunch charitable giving into alternate years using a Donor-Advised Fund, and check whether the 0.5% floor is quietly eating a small annual gift

5. Update Form W-4. If your deduction position changed materially from last year, your withholding is now wrong in one direction or the other. Work out the Step 4(b) figure to enter rather than guessing — the 2026 form's deductions worksheet has lines for the SALT cap, the 7.5% medical floor, the 0.5% charitable floor and the senior deduction, and getting them right is the difference between a refund and a surprise bill in April 2027

Key Takeaways

1. The OBBBA SALT cap of $40,400 for 2026 is the change that moves people across the line — but it phases down above $505,000 of MAGI and reverts to $10,000 after 2029.

2. 2026 standard deductions are: Single $16,100 / MFJ $32,200 / HOH $24,150, plus $2,050 (single or HOH) or $1,650 per spouse (joint) at 65+, plus OBBBA's $6,000-per-person senior deduction which you get either way.

3. Itemize if SALT + mortgage interest + charitable giving + medical expenses exceed your standard deduction — and value the decision at the gap times your marginal rate, not the total times your top bracket.

4. Two new-for-2026 charitable rules cut in opposite directions: itemizers lose the first 0.5% of AGI of giving; non-itemizers gain a $1,000/$2,000 above-the-line deduction they did not have.

5. Bunching through a Donor-Advised Fund is the highest-leverage move for borderline households, and 2026's charitable floor makes it slightly more valuable than it was.

6. Investment income changes the answer. If your income is long-term capital gains and qualified dividends, your deductions are worth 15% or 20%, not 24% or 32% — sometimes less than half what an ordinary-income household saves on the identical deductions.

Run the numbers for your own situation. If you own a home in a high-tax state and give to charity, itemizing is likely; if you rent, or your mortgage is late in its life, the standard deduction almost certainly wins.

FAQ

I itemized last year. Do I have to itemize again this year?

No. The choice is made fresh every year on the return you file, and nothing carries over. In fact you should expect it to flip at some point: the standard deduction rises with inflation every year while mortgage interest falls as the loan amortises, so a household that itemized in 2020 may well be better off with the standard deduction now without anything having changed in their life. Recalculate annually. The one asymmetry to know is between spouses filing separately — if one spouse itemizes, the other must itemize too, even if their own deductions are close to nothing.

Can I take the standard deduction and still deduct charitable donations?

Yes, and this is new for 2026. OBBBA restored a permanent above-the-line charitable deduction of $1,000 for single filers and $2,000 for joint filers that you claim on top of the standard deduction. There is a second route for anyone over 70½: a qualified charitable distribution sends money straight from an IRA to a charity, never appears in your income at all, and counts toward your required minimum distribution — which for most retirees is worth more than any Schedule A deduction, because keeping income off the return also protects Social Security taxability and Medicare IRMAA thresholds.

Does the SALT cap apply per person or per return?

Per return, which penalises married couples. A married couple filing jointly shares one $40,400 cap; two single people living in the same situation get $40,400 each. Filing separately does not fix it — the cap is halved to $20,200 each for married-filing-separately, so the total is identical, and MFS costs you other benefits besides. This is the "marriage penalty" in the SALT cap, and it survived OBBBA intact.

My medical bills were huge last year. Why didn't they help?

Because only the portion above 7.5% of your AGI counts, and then only if your total itemized deductions beat the standard deduction. On $100,000 of AGI, the first $7,500 of medical spending is invisible; $12,000 of bills produces a $4,500 deduction, which on its own is nowhere near the $32,200 joint standard deduction. Medical expenses realistically only change the answer when they are catastrophic relative to income — a year with a long hospitalisation, a nursing home, or a household whose income dropped at the same time their costs rose. If you are in that situation, note that the deduction includes insurance premiums, long-term care, mileage to appointments, and home modifications made for a medical reason, not just the bills themselves.

Should I prepay next January's property tax in December to itemize this year?

Usually not any more, because the SALT cap makes it self-defeating. If you are already at or near $40,400 of SALT, an extra prepayment is simply not deductible — you have accelerated a payment for nothing. Prepaying only helps if your SALT total is comfortably below the cap and the acceleration is what pushes you over the standard deduction, which is a narrow window. Charitable bunching is the better lever for the same goal: it has a much higher ceiling (60% of AGI) and, through a DAF, does not force you to hand the money to the charity all at once.