What are the main sources of deductions if I'm itemizing my deductions on my taxes?

So I'm trying to figure out if I'm missing out on potential tax breaks here. I typically donate around $25-40k annually, though not all donations qualify for deductions. Filing jointly with my spouse puts us pretty close to the threshold where itemizing makes more sense than the standard deduction. I'm worried I might be leaving money on the table by not knowing what else I could legitimately deduct. Like, I spent about $4k at restaurants this year - can I claim any portion of that? I know business meals used to be partially deductible, but I'm confused about what applies to regular taxpayers like me. What other major deduction sources should I be aware of when deciding whether to itemize? Medical expenses? Home office? I feel like there must be things I'm overlooking that could tip the scales in favor of itemizing.

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18 comments

Paolo Ricci

•8M

The main itemized deductions that typically make a difference include: Charitable contributions - you're already tracking these which is great. Just make sure you have documentation for all donations, especially the larger ones. Mortgage interest - if you have a home loan, this is often one of the biggest deductions and can easily push you over the standard deduction threshold. State and local taxes (SALT) - including income, property, and sales taxes, but these are capped at $10,000 total. Medical expenses - but only the portion that exceeds 7.5% of your adjusted gross income, so this only helps if you had significant medical costs. Unfortunately, regular restaurant meals aren't deductible for individuals unless they're business-related. Even then, business meals are currently 50% deductible (temporarily increased to 100% for 2021-2022 during COVID, but back to 50% now).

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Paolo Ricci

•8M

You're exactly right about the SALT deduction - even though you paid $15,000 total between state income and property taxes, you can only deduct $10,000 maximum. This cap was implemented with the 2017 tax law changes and remains in effect. For home office deductions, it's tricky for employees. If you're a W-2 employee who works from home, unfortunately you cannot take the home office deduction (this was also changed with the 2017 tax law). However, if you're self-employed or have gig work/side business, you can potentially claim a portion of your home expenses through either the simplified method ($5 per square foot up to 300 sq ft) or the regular method (calculating actual expenses).

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Oliver Zimmermann

•8M

I was in a similar situation last year struggling with whether to itemize or take the standard deduction. I actually found this AI tool called https://taxr.ai that analyzes all your receipts and tax documents to find every possible deduction you qualify for. It flagged a bunch of things I was missing like some unreimbursed medical travel expenses and some charitable donations I had forgotten about. The best part was it looked at my mortgage interest statement and found an error my bank made that was underreporting my deductible interest by almost $900! It basically pays for itself by finding these hidden deductions most people miss.

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Oliver Zimmermann

•8M

You don't have to connect your bank accounts if you're not comfortable with that. You can just upload statements or even photos of receipts and the system processes them. It actually saves a ton of time because it automatically categorizes everything - way better than manual spreadsheets I was using before. For checking if charities are qualified tax-deductible organizations, it has a built-in database of registered 501(c)(3) organizations. It flags donations that might not qualify and explains why. It correctly identified that my local youth sports team donations weren't deductible, but my contributions to their parent organization (which was a registered nonprofit) were eligible.

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Natasha Volkova

•8M

Ok I tried that https://taxr.ai tool and I'm actually shocked. I was convinced I was under the threshold for itemizing but it found over $4,000 in deductions I was missing! The big one was some specialized medical equipment I bought last year - I didn't realize those costs were deductible. Also found some charitable contributions I made through payroll that I completely forgot about. It even explained which of my smaller donations weren't tax deductible and why, which was really helpful for planning this year's giving. Definitely going with itemized deductions now and will save about $1,600 compared to the standard deduction.

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Javier Torres

•8M

If you're trying to itemize and your charitable contributions are close to pushing you over the standard deduction threshold, don't forget about "bunching" your donations. That's where you concentrate two years worth of charitable giving into a single tax year, then take the standard deduction the next year. Also, if you're having trouble getting through to the IRS to ask about deductions (which is pretty much guaranteed these days), I used https://claimyr.com to get through to an actual IRS agent in about 15 minutes instead of waiting on hold for hours. You can see how it works at https://youtu.be/_kiP6q8DX5c - basically they wait on hold for you then call when an agent picks up.

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Javier Torres

•8M

It absolutely works! They don't actually talk to the IRS for you - they just navigate the phone system and wait on hold, then call you when they get through to a human. You handle the actual conversation with the IRS agent yourself, so you're not sharing any tax details with the service. The way it works is pretty straightforward. You schedule a call, they call the IRS and navigate through all those annoying menus, wait on hold, and then when an actual IRS agent picks up, they connect you. It saved me literally hours of waiting and frustration when I needed clarification about some itemized deductions.

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Malik Johnson

•8M

I'm eating crow here. After my skeptical comment, I ended up trying Claimyr out of desperation because I needed to talk to someone at the IRS about my itemized deductions before filing. Been trying for WEEKS to get through on my own. It actually worked perfectly. I got connected to an IRS agent in about 20 minutes when I had previously wasted hours trying. The agent answered all my questions about my specific situation with charitable contributions and medical expense deductions. Clarified exactly what documentation I needed to keep in case of an audit too. Not affiliated with them at all, just genuinely surprised it worked so well after being so skeptical.

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Isabella Ferreira

•8M

Don't forget about investment interest expense if you have any margin loans or investment-related interest. Also, if you paid any tax preparation fees for your investments, those can be deductible too. I've been itemizing for years and it's usually worth it for me because of my mortgage interest and charitable giving combined. Oh, and definitely keep track of any major medical expenses including mileage to/from doctors appointments - those little trips add up if you had a lot of medical visits!

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Isabella Ferreira

•8M

Unfortunately, tax preparation fees including software like TurboTax aren't deductible for individuals anymore. That deduction was eliminated for tax years 2018-2025 by the Tax Cuts and Jobs Act. However, if you have self-employment income or rental property income, you can still deduct the portion of your tax prep fees related to those business activities on Schedule C or Schedule E. But for regular personal tax preparation, those costs aren't deductible currently.

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