Quick question - what about internet and phone bills? Are those treated the same way as property taxes and insurance (partial based on sq footage) or can I deduct more of those since they're more directly used for business purposes?

One thing I learned the hard way - make sure you're using the space "exclusively" for business if you want to claim the home office deduction. The IRS is really strict about this. If you sometimes use that room to watch TV, store personal stuff, or let guests sleep there, you can't claim it as a business expense. I got audited a few years back because I claimed my spare bedroom as an office, but I also had a pullout couch in there for guests. The auditor disallowed the entire deduction because it wasn't exclusively business use. Now I have a dedicated office space that's only used for work - no exceptions. Also, keep detailed records of your square footage measurements and take photos showing the business use. If you get audited, they'll want proof that the space is truly dedicated to business activities only.

Has anyone used TurboTax to report a home sale? I'm trying to figure out if their interview process walks you through all this stuff about selling expenses and basis adjustments automatically.

One thing I haven't seen mentioned yet is the importance of keeping detailed records even if you don't think you'll need them. I sold my primary residence two years ago and was well under the exclusion limit, so I almost didn't bother tracking my selling expenses. But then I ended up buying another house and selling it within a year due to a job relocation - suddenly I was in a situation where those expenses from the first sale became relevant for calculating my overall tax situation across multiple transactions. Also, if you're close to retirement age or think you might be selling again soon, those selling expense records could become valuable later. The IRS generally requires you to keep tax records for 3-7 years, but for real estate transactions, I'd recommend keeping everything permanently. You never know when you might need to reference your basis calculations for future property decisions or if the IRS comes asking questions years down the line. Even though it seems like extra work when you're under the exclusion, maintaining good records is just good practice and costs you nothing but a little organization time.

I had a very similar situation last year with municipal bonds purchased in December 2023. What really helped me was creating a simple spreadsheet to track all my bond purchases with accrued interest, including the purchase date, accrued interest paid, and expected first payment date. The key thing I learned is that the IRS views accrued interest as a "return of capital" rather than a deduction. You're essentially getting back money you paid to the previous bondholder for interest they earned but hadn't collected yet. This is why it must be reported in the same year you receive the actual interest payment - because that's when you're reporting the income that needs to be adjusted. For your March 2025 payment, you'll report $750 as interest income and then subtract the $125 accrued interest as a negative adjustment on Schedule B. Make sure to keep your purchase confirmation showing the accrued interest amount - the IRS may ask for documentation if they have questions about the adjustment.

I've been dealing with a similar situation with TIPS (Treasury Inflation-Protected Securities) that I bought in late 2024. The accrued interest timing issue becomes even more complex with TIPS because of the inflation adjustments, but the basic principle is the same. One thing I learned from my tax preparer is to keep detailed records not just of the accrued interest amount, but also the exact settlement date and the interest payment schedule. This helps if you ever need to explain the timing to the IRS. She also mentioned that if you have multiple bonds with different accrued interest amounts, you should list each one separately on Schedule B rather than lumping them together - it makes the return clearer and less likely to trigger questions. For anyone using tax software, I found that H&R Block's premium version handles this better than TurboTax. It has a specific section for bond accrued interest adjustments that walks you through the process step by step. But honestly, after reading all these responses, it sounds like manually tracking everything in a spreadsheet and then entering the adjustments yourself is the most reliable approach regardless of which software you use.

For a super simple return with just an HSA, I've been using H&R Block's free online version for years. They still include HSA Form 8889 in their free tier unlike TurboTax. Their interface isn't as slick but it gets the job done without the surprise fees.

I went through this exact same frustration last year! TurboTax definitely changed their policy on HSAs - it used to be included in the free version. The $120 total cost is outrageous for such a simple return. I ended up switching to FreeTaxUSA and it's been great. HSAs are handled completely free on the federal return, and state filing is only $15. The interface isn't as flashy as TurboTax but it walks you through everything clearly. I've used it for two years now with my HSA and haven't had any issues. The IRS Free File program is also worth checking if your AGI is under $73K - several participating companies offer completely free filing including HSA support. Don't let TurboTax's marketing fool you into thinking you need their overpriced service for something this basic!

Small tip that saved me once - check your email from around the time you filed last year. Sometimes confirmation emails from Free Fillable Forms or the IRS have useful reference numbers or confirmation details that can help expedite getting copies. Also, if your refund was direct deposited, check your bank statements from that time period - the exact refund amount can sometimes help your tax preparer cross-reference and confirm your AGI.

Don't panic! You're definitely not alone in this situation. I made the exact same mistake a few years back with Free Fillable Forms - it's surprisingly common since they don't automatically save or email your completed returns. Here's the good news: your tax preparer likely doesn't need the actual return copies to complete your 2024 taxes. The main things they need are your prior year AGI (Adjusted Gross Income) and any carryover items like capital losses or charitable contribution carryovers. If you have your W-2s, 1099s, and other tax documents from last year, an experienced preparer can calculate your AGI pretty accurately. For the official documentation, definitely start with the free IRS transcript online at irs.gov/transcripts - it's immediate if you can verify your identity online. For DC, try MyTax.DC.gov first before calling. The April 15th deadline is definitely doable! Your preparer can work with what you have now and you can get the official transcripts for your records later. The key is having those income documents from 2023, which it sounds like you do have.