Just a heads up for first-time filers - make sure you keep really good records of everything! I messed up my first time filing with stock transactions because I didn't save some important confirmation emails from when I sold some random penny stocks. Also check if any of your trades were marked as "covered" vs "noncovered" on your 1099-B. Noncovered positions might not have complete basis info reported to the IRS, which means more work for you.

This is such a helpful thread! As someone who also got overwhelmed with investment tax forms this year, I wanted to add one more tip that really helped me understand the relationship between Form 8949 and Schedule D. Think of it like this: if you were reporting charitable donations, you'd list each individual donation on a detailed worksheet, then summarize the total on Schedule A. Form 8949 is like that detailed worksheet for your stock trades - every buy, every sell, with all the specifics. Schedule D is like the summary line that goes on your main return. For wash sales specifically, the IRS wants to see that detailed transaction history on Form 8949 because they need to verify that the disallowed loss was calculated correctly and that you're not trying to claim a tax benefit you shouldn't get. One thing I learned the hard way - if you have a lot of transactions, you can actually group similar ones together on Form 8949 instead of listing every single trade individually. Check the instructions for when this is allowed, as it can save you tons of time!

Has anyone had the IRS apply their overpayment to a state tax debt? I heard they can do that but not sure if its automatic or if you have to request it?

I went through something very similar last year with back taxes from 2021. The IRS will definitely refund any overpayment automatically - no special forms needed. What helped me was creating an online account at irs.gov so I could track the status of my payment and see exactly how they calculated the penalties and interest. One thing to keep in mind: if you made the payment recently, it can take up to 6-8 weeks for them to fully process everything and issue the refund. They have to apply your payment, calculate the exact amount owed as of the payment date, and then process the overpayment. You should receive a notice explaining their calculations before the refund arrives. Also, double-check that you don't have any other outstanding federal debts (like student loans) because they might offset your refund against those before sending you the money. Good luck!

Is there a cutoff on how much profit is tax free? Im in a similar situation but made about $175k on my house that I lived in for 3 years. Will all of that be exempt?

Great question about the primary residence exemption! You're absolutely right that there's a 2-out-of-5-years rule, and you definitely qualify. Since you lived in the house as your primary residence for nearly 5 years (2019-2023), you've more than met the residency requirement. The fact that you're renting instead of buying another home immediately doesn't matter at all for the exemption - there's no requirement to reinvest the proceeds. However, since you made $320k in profit, you'll want to consider the exemption limits: $250k if you're single, or $500k if you're married filing jointly. If you're single, you'd owe capital gains tax on $70k of your profit ($320k - $250k exemption). Don't forget to add any qualifying home improvements you made during ownership to your cost basis, as this could reduce your taxable gain. Things like major renovations, new HVAC systems, or structural improvements can be added to what you originally paid for the house. Also remember that since you owned the home for more than a year, any taxable portion will be subject to long-term capital gains rates (typically 0%, 15%, or 20% depending on your income level), which are generally more favorable than ordinary income tax rates.

Community wisdom on avoiding SBTPG: • Most tax prep companies use either SBTPG or Republic • H&R Block uses Axos Bank (mixed reviews) • TurboTax uses SBTPG exclusively • Jackson Hewitt uses both SBTPG and Republic • Direct deposit to your own account is always fastest • Paying prep fees upfront avoids these banks entirely I've been filing for 15+ years and learned this the hard way. These refund transfer services only exist to take fees from people who can't pay upfront.

Just went through this nightmare with SBTPG myself this year! My refund was delayed 18 days and their customer service was absolutely terrible. Here's what I'm doing differently next year: I'm switching to FreeTaxUSA and paying the small fee upfront ($14.99 for state filing) to get direct deposit straight to my bank account. No third-party banks, no transfer fees, no delays. Another option if you want to stick with Jackson Hewitt - ask them specifically about their "no bank product" option where you pay fees upfront. Some locations don't advertise this but they all offer it. You just have to be very clear that you want direct deposit to YOUR account, not through any refund transfer service. The key is being prepared to pay those prep fees out of pocket instead of having them deducted from your refund. It's worth it to avoid the SBTPG headache!

I'd strongly recommend going the personal donation route rather than trying to transfer it to your business first. As others have mentioned, the IRS takes a dim view of last-minute asset transfers just to claim business deductions. For your $4,000-5,000 boat, you'll need Form 8283 and a qualified appraisal since it's close to the $5,000 threshold. Don't try to lowball the value to avoid the appraisal requirement - that's a red flag for audits. Get a marine surveyor to give you a proper fair market value assessment. Also, keep detailed records of the boat's condition with photos and any maintenance records you have. The IRS will want to see that your valuation is reasonable given the actual state of the vessel. Since you mentioned it's "falling apart," make sure your appraisal reflects that reality. One last tip - if the charity ends up selling the boat for significantly less than your claimed value (which often happens with boats in poor condition), your deduction will be limited to the actual sale price, not your appraised value.

Just wanted to add something that might help with the documentation side of things - make sure you get a receipt from the charity that includes specific language about the donation. The IRS requires the receipt to state whether you received any goods or services in return for your donation (which should be "no" for a straight boat donation). Also, since you mentioned the boat is in poor condition, document everything thoroughly with dated photos showing the specific issues - hull damage, engine problems, interior wear, etc. This will be crucial if the IRS ever questions your valuation. I learned this the hard way when I donated an old RV and didn't have enough documentation of its condition. One more thing - if you do go the personal donation route and itemize, remember that charitable deductions are subject to AGI limitations. Non-cash donations to public charities are generally limited to 50% of your adjusted gross income, with any excess carrying forward for up to 5 years. Given your boat's value, this probably won't be an issue, but it's worth keeping in mind.