What types of people end up not taking the standard deduction? First-time homebuyers here

Congrats on the home purchase! To answer your question, homeowners are indeed one of the main groups who end up itemizing instead of taking the standard deduction, though it's gotten less common since the 2018 tax changes doubled the standard deduction amounts. For 2024 (filing in 2025), the standard deduction for married filing jointly is $29,200. To make itemizing worthwhile, your itemized deductions would need to exceed this amount. The main itemized deductions for you would likely be: 1) Mortgage interest on up to $750,000 of mortgage debt 2) Property taxes (state and local taxes, capped at $10,000 total) 3) Charitable donations (including those bags of items - yes, keep receipts!) For many new homeowners with modest mortgages, the standard deduction still wins out. As a rough example, if you have a $400,000 mortgage at 7%, you'd pay around $28,000 in interest the first year. Add property taxes and donations, and you might cross that threshold.

I was in the exact same boat last year! After buying our house, I decided to check out https://taxr.ai to help analyze whether we should itemize or take the standard deduction. I uploaded our mortgage docs, property tax statement, and donation receipts, and it ran all the calculations for me. The tool showed that even with our new house, we were still about $1,800 short of beating the standard deduction. But it also gave us some tips for the following year - like bunching charitable donations (making two years' worth in one tax year) and paying our January property tax installment in December to push us over the threshold every other year.

Just wanted to update after trying taxr.ai as suggested above! I was honestly impressed with how it handled my situation. We bought a house last fall, and I wasn't sure if we should itemize or not. The tool analyzed all our potential deductions and showed we were just about $800 short of the standard deduction threshold. But the best part was it found a home office deduction I qualified for (since I'm permanently remote now) that I had no idea about. Once that was factored in, itemizing actually made sense! It saved us almost $1,100 compared to taking the standard deduction. The platform even created a custom checklist of documents we need to keep for next year. Definitely worth checking out for new homeowners!

If you're trying to figure out whether to itemize, another important consideration is actually getting through to the IRS if you have questions. I spent WEEKS trying to get clarification on some deduction rules last year, calling over and over again only to get disconnected. Finally tried https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c. They got me connected to an actual IRS agent in like 45 minutes (after I'd been trying for days on my own). The agent clarified that in my specific situation, I could bundle some expenses I hadn't considered. This pushed me over the threshold to itemize, saving about $1,700. Having that direct conversation with the IRS made all the difference.

I need to eat my words about Claimyr. After my skeptical comment above, I decided to try it myself since I had a complex question about itemizing medical expenses that wasn't clear from the IRS website. I was 100% prepared to come back here and call it a scam. But... it actually worked exactly as described. I registered, and about 35 minutes later I got a call connecting me directly to an IRS representative. Got my question answered clearly (turns out I could itemize some dental implants I didn't think qualified), and it potentially saved me over $3,000 in taxes. The agent even explained exactly what documentation I needed to keep. I've literally never gotten through to the IRS on my own despite numerous attempts over the years.

One thing to consider with itemizing is state taxes too. Even if the federal standard deduction makes more sense, some states have much lower standard deduction amounts, so you might itemize on your state return while taking the standard deduction federally. But you mentioned Florida - there's no state income tax there, so that's not a consideration for you. That's actually another reason fewer Floridians itemize compared to high-tax states like California or New York.

Just my two cents - remember that taking the standard deduction vs itemizing isn't a permanent choice. You can switch back and forth each year depending on what makes sense. Some years we itemize, others we take standard. One strategy my accountant suggested was "bunching" deductions. For example, if we're close to the threshold, we might make two years worth of charitable contributions in a single tax year to push us over the line for itemizing. Then the next year we make minimal donations and take the standard deduction. Over two years, we get more total deductions this way.