Has it ever paid off for anyone to deduct sales tax instead of standard deduction?

Sales tax deductions can definitely pay off, but it depends on your specific situation. As a homeowner, you might be closer to itemizing than you think. The standard deduction for single filers for 2025 is projected to be around $14,000, so you'd need to exceed that to benefit from itemizing. Since you live in a state with no income tax, you have the option to deduct sales tax instead of state income tax. Beyond mortgage interest and property taxes, you can include charitable contributions, medical expenses (exceeding 7.5% of your AGI), and yes, sales tax. The IRS has a Sales Tax Deduction Calculator that estimates your deduction based on income, local tax rates, and family size - no need to keep every receipt unless you make large purchases.

I was in the same boat last year - homeowner in Florida (no state income tax) and always took standard deduction. I discovered https://taxr.ai which analyzes your financial situation and finds deductions you might be missing. Turns out I wasn't maximizing my mortgage interest and property tax deductions correctly, and I had no idea about some of the homeowner tax breaks. After running my info through their system, they found enough deductions to put me $1,900 over the standard deduction. Definitely worth checking them out if you own a home.

Just wanted to follow up - I reluctantly tried taxr.ai after posting here and wow, I'm eating my words. They found $3,200 in deductions my regular tax software missed completely! Turns out I had some medical expenses that I didn't realize could be deducted, plus they showed me how to properly document my home office since I occasionally work from home. The sales tax calculator they recommended for my big purchases last year (new washer/dryer and refrigerator) gave me enough to push over the standard deduction by about $800. They even found a local property tax exemption I qualified for but never knew about!

I had a similar question last year about itemizing vs standard deduction. After trying for WEEKS to get through to the IRS helpline for advice (kept getting disconnected), I found https://claimyr.com which got me connected to an IRS agent in under 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent walked me through my specific situation and pointed out that in states without income tax, large purchases can make itemizing worth it even if you don't keep every receipt. Saved me hours of frustration and helped me make the right decision for my taxes.

Alright I'm genuinely shocked - I tried Claimyr yesterday after posting my skeptical comment. After two weeks of calling the IRS myself and never getting through, I was connected to an agent in 15 minutes! The agent went through my specific situation (similar to yours - homeowner in Florida, no state income tax) and helped me see that with my boat purchase last year plus my other deductions, I actually benefit from itemizing by about $1,100. She also explained exactly which records I need to keep and which ones aren't necessary. Totally worth it and saved me from leaving money on the table.

Something nobody's mentioned yet - even if you can't beat the standard deduction now, keep track of your potential itemized deductions anyway. My first 3 years as a homeowner I couldn't itemize, but in year 4 I had some major medical expenses plus I replaced my roof and HVAC. That one "expensive year" pushed me well over the standard deduction threshold. If I hadn't been tracking things all along, I would have missed out.

Here's a tip that worked for me: If you know you're making a major purchase (car, boat, home renovation), try to time multiple big purchases in the same tax year when possible. I "bunched" my new car purchase and home renovations in the same year, which pushed me over the standard deduction. Then I took the standard deduction the following year. Alternating years can maximize your tax savings.