Oh that's a huge relief! I was stressing about trying to track down decades-old purchase records. So I just need to document what the value was on the date he passed away? That's much easier since it was only last year and I can look up the historical prices online. Do I need any special documentation to prove that value in case of an audit? Or is just having the date of death and the corresponding stock values enough?

Yes, just document the closing price on the date of death. For additional protection, I suggest taking screenshots or printing the historical price information from a reputable financial website and keeping that with your tax records. If the estate was large enough to file an estate tax return (Form 706), that document would also have the valuation information and would be excellent documentation. But for most people, good records of the date of death values from reliable sources are sufficient for audit protection.

The IRS generally keeps transcripts available for the current tax year and the prior three years through their online system. But they actually maintain records for much longer - typically 7-10 years. For 2016 records, you'll probably need to complete Form 4506-T and mail or fax it to request older transcripts. Or call them directly. There's usually no fee for transcripts (unlike actual tax return copies which cost $50 each).

14 I did equipment financing for my food truck equipment. The key difference is whether it's structured as a true lease or a loan. With a true lease, you deduct the payments themselves as rent expenses. With financing that's basically a loan, you own the equipment and deduct through depreciation or Section 179. My accountant had me review the contracts to determine which type I had - turns out mine was actually a loan despite being called a "lease," so I got to deduct the equipment value upfront with Section 179.

7 That's super helpful, thanks! I didn't realize the contracts might use confusing terminology like calling a loan a "lease." I'll make sure to have someone review the actual terms before signing. Did you find any significant difference in interest rates between traditional small business loans and equipment financing?

4 Exactly right! The principal isn't deductible (that's what you're getting the equipment deduction for), but the interest is absolutely a separate business expense. Good catch - lots of new business owners miss this one.

14 Does Direct File work if you have multiple W-2s and some 1099 interest? I've got 3 jobs and a savings account.

16 Direct File should work just fine with multiple W-2s and 1099-INT forms for interest income. The 2025 version has been expanded to handle most common simple to moderate tax situations. What it still doesn't support well are things like self-employment income, rental properties, or extensive investment transactions. But for your situation with 3 jobs and a savings account, you should qualify without issues.

11 H&R Block's free version is slightly better than TurboTax's but they still upsell HARD once you have anything beyond basic W-2 income. I tried them last year thinking I'd save money but ended up paying almost the same as TurboTax would've charged when they forced me to upgrade for my stock sales. FreeTaxUSA or Cash App Taxes are genuinely free alternatives that don't pull the bait-and-switch.

Terrible advice. The IRS can look back several years if they decide to audit you. Better to do things right the first time than risk problems later. I learned this the hard way.

You're right that documentation is ideal, but I'm just sharing my real-world experience. The IRS audits less than 1% of tax returns for people making under $200k annually. I agree it's better to do things properly, especially for larger amounts or if you're concerned about potential audit flags in your situation. My point was simply that many family loans happen informally without issues. That said, if someone has the option to document things properly from the beginning, they absolutely should.

Promissory notes are definitely the way to go! I'm an accountant (not giving professional advice) and this is what I recommend to friends and family. It doesn't need to be complicated - just the amount, dates, payment terms, signatures. Keep it with your tax records.

I did use TurboTax but paid their fee with my credit card, not out of my refund. And definitely didn't take any refund advance loans. Looking at my transcript again, it clearly shows the full $4,089 as the amount that should have been refunded. So confusing!

That is strange then. One last thing to check - did you look at your tax return transcript or your account transcript? The account transcript would be more accurate for refund information as it shows all transactions on your account. Sometimes the numbers can look similar but mean different things. If the account transcript definitely shows $4,089 as the refund amount and you only got $3,717, then something's definitely off and you'll need to contact the IRS directly. Might be worth using one of those services others mentioned since the phone lines are so jammed.

This is what happened to me too. Missing $540 from my refund, turns out I had forgotten about an outstanding state tax bill from two years ago. The really annoying part is that the notice explaining it came almost 3 weeks AFTER the reduced refund hit my account!