Thanks for your insight. The trustee hasn't been very communicative about the tax details. Is this something I can pursue myself as a beneficiary, or does it have to be initiated by the trustee? I'm worried because my brother (the trustee) doesn't seem to understand the tax implications here.

Unfortunately, only the trustee has the legal authority to file amended tax returns for the trust. As a beneficiary, your best approach is to formally document your concerns in writing to the trustee, possibly with information from a tax professional explaining the step-up basis rules. If the trustee is unresponsive or unwilling to correct potential errors, you might need to consult with an estate attorney about your rights as a beneficiary. Trustees have a fiduciary duty to manage the trust properly, which includes not overpaying taxes. A letter from an attorney explaining this fiduciary duty might motivate them to take appropriate action. Given the potential tax overpayment amount, this is definitely worth pursuing.

Thats a really important point about irrevocable vs revocable trusts! My family learned this the hard way. Worth checking the trust documents carefully to confirm what type of trust it was. The tax conseqeunces are huge.

That's actually not a bad idea if they're local! My old job was cool about it. The HR lady even apologized and said a bunch got lost in the mail. Way better than waiting on hold with the IRS.

This is great advice, thank you! I'll start keeping track of my attempts to get it. Do you think a simple log with dates and times of calls would be sufficient, or should I be sending emails so I have written proof?

Email is definitely better because it gives you a clear paper trail. Send a polite email to HR or payroll requesting your W-2, mentioning that you haven't received it yet and the January 31st deadline has passed. If you call, follow up with an email summarizing the call ("As we discussed on the phone today..."). For extra protection, if they don't respond to regular emails after a week, send a certified letter with return receipt. This proves they received your request. The IRS takes this stuff seriously, and if your employer is systematically failing to provide W-2s, your documentation could help with any potential investigation.

What about if you have 1099 income but it's really small? Like I made only about $3k from a side gig last year. Is that worth paying someone for?

For small 1099 income around $3k, you can probably still handle it yourself using tax software. You'll need to file Schedule C to report the income and expenses, but most tax programs walk you through this process well. Make sure you track all legitimate business expenses to offset that income! The key is keeping good records of your business expenses throughout the year. Even simple things like a portion of your cell phone bill, home internet, or mileage can be deductible if used for your side gig. You'll also need to pay self-employment tax on that income (about 15.3%), but you can deduct half of that on your return.

I used to think the same until I hired a CPA after having kids and buying a house. She found almost $2,800 in deductions and credits that TurboTax missed! Paid for herself many times over. Software only finds what you know to tell it about.

1 Thank you so much for this detailed list! I just double-checked my receipts and noticed one is missing the statement about goods/services. Should I request a corrected receipt before filing?

14 Absolutely request a corrected receipt before filing. That statement about whether goods or services were provided is actually required by the IRS for any donation over $250, and without it, your deduction could be disallowed in an audit even if the donation was legitimate. Contact the organization right away and explain that you need a corrected acknowledgment letter for tax purposes. Most nonprofits are very familiar with this requirement and will quickly provide an updated letter with the proper language. Be specific about what's missing so they can correct it properly.

23 In my experience (donated about 40% of income last year), my refund was delayed by about 3 weeks compared to previous years. Not sure if it was related to the donation or just general IRS backlog though.

Oh that's actually really clever! I never thought about checking file size. Does this work even if you e-filed though? I don't think I printed out all the forms but maybe the PDF would still be different sizes?

Yes, it works even if you e-filed! The PDF you get from your tax software after filing (usually called something like "2020_Tax_Return.pdf") will include all forms that were submitted with your return, even if you never printed them out. The file size difference comes from all the additional schedules and worksheets that get generated when you itemize. Besides Schedule A itself, there are often supporting documents for medical expenses, property taxes, mortgage interest, charitable contributions, etc. So the PDF generally ends up noticeably larger than years when you took the standard deduction.

That's unusual but I think I know what happened. The "Schedule A" checkmark on line 8 probably means you filled out Schedule A to compare your itemized deductions against the standard deduction. But since line 12 shows exactly $24,800 (the standard deduction amount for married filing jointly), you ultimately took the standard deduction because it was higher than your itemized amount would have been. TurboTax and other software often complete Schedule A as part of the process even if you end up taking the standard deduction, just to determine which gives you the better outcome.