I just use last year's answers as the starting point and ask if anything has changed. For new clients, I have a checklist of the most common "yes" answers and focus on those. Nobody has time to go through 20+ questions line by line that 99% don't apply to most small businesses anyway. Let's be real - most of Schedule B is irrelevant for standard partnerships. I focus on the ones that matter: foreign accounts, foreign partners, publicly traded partnerships, etc. The rest I just mark "no" based on my understanding of the client's business. In 15 years, never had an issue.

Has anyone tried using tax software's built-in organizers for Schedule B? I use Lacerte and their partnership organizer includes simplified versions of the Schedule B questions, but I find clients still get confused by them.

Lot of good tax advice here but im surprised nobody mentioned checking if the account might have unreported sales! If your grandfather or the custodian ever sold shares and reinvested, those would trigger capital gains that shoulda been reported. id get a complete transaction history from fidelity going back however many years u can. might be surprised what happened in that account!

One thing I'd add that might ease some of your anxiety - most UTMA accounts with just dividend income from a single stock like Amazon typically don't generate huge tax liabilities, especially if the account wasn't actively traded. Amazon's dividend yield is pretty low (around 0.5-1% historically), so even if the account value is substantial, the annual dividend income might be relatively modest. That said, definitely get those records from Fidelity and consider working with a tax professional for the amended returns. Many CPAs have experience with exactly this type of situation since forgotten UTMA accounts are more common than you'd think. They can also help you understand if you qualify for any penalty relief programs for first-time filers or reasonable cause exceptions. Also worth noting - once you get this straightened out and transfer the account to your name, you'll have more control over the tax timing. You can choose when to sell shares (if at all) to manage your capital gains in years when your income might be lower.

Anyone have recommendations for good tax software for beginners? I've been using whatever free option I can find each year but they're all confusing.

I learned taxes by making a ton of mistakes lol. Seriously though, just start doing them yourself with tax software. Even if you mess up, the IRS usually just sends a letter and you fix it. One year I completely forgot to report my stock sales and they just sent me a bill for the difference plus a small penalty. NBD. The best way to learn is by doing!

Does anyone know if IRS Form 3922 helps with these calculations? My employer provides this form for ESPP purchases but I'm not sure how to use it for tax filing.

This is exactly the kind of confusion that trips up so many people with ESPP taxes! I went through the same thing last year and made the mistake of using the subscription FMV instead of the purchase date FMV for my disqualifying disposition. The key thing to remember is that with a disqualifying disposition (selling within one year), you're essentially being taxed on the full "bargain element" - which is the difference between what the stock was actually worth when you bought it versus what you paid for it. In your case, that's $89.50 - $65.42 = $24.08 per share. The 15% discount from the subscription price is just how the ESPP program works, but for tax purposes, the IRS cares about the actual market value on the day you purchased the shares. Your ESPP Disposition Summary is correct showing $758.78 as ordinary income. One thing that helped me was keeping detailed records of all the dates and prices involved. The timing of ESPP purchases can be confusing because there's the offering period start date, the purchase date, and then your sale date - and different FMV prices apply to each for different parts of the calculation.

Don't forget to take photos of the wheelchair from multiple angles before donating! I made this mistake when donating medical equipment and had a hard time during an audit because I couldn't show exactly what condition it was in. Close-ups of any model numbers, special features and the general condition are really important. Also make sure the receipt you get from the charity specifically describes the item as a "specialized tilt wheelchair" rather than just "medical equipment" or "wheelchair." The more specific, the better for tax purposes.

I went through something very similar when I donated my mother's lift chair and walker last year. The IRS Publication 561 specifically covers determining value for donated property and is really helpful for situations like yours. For medical equipment donations, I found that documenting your research process is just as important as the final value you choose. I created a simple spreadsheet showing comparable items I found online with their asking prices, conditions, and ages. Then I calculated an average and adjusted based on my item's specific condition and features. Since your wheelchair has specialized tilt functions, it likely holds value better than a standard wheelchair. I'd suggest looking specifically for tilt wheelchairs in your research rather than just any wheelchair. The specialized features command higher resale values. One thing that really helped me was calling a local medical equipment rental company and asking what they typically sell their used tilt wheelchairs for. They were surprisingly helpful and gave me a realistic range based on age and condition. This gave me an additional data point beyond just online listings. Keep all your research documentation - screenshots of comparable sales, notes from any calls you make, photos of the wheelchair, and your calculation method. The IRS wants to see that you made a good faith effort to determine fair market value, and thorough documentation shows exactly that.