Has anyone used the Taxpayer Advocate Service for HSA distribution issues specifically? Just wondering if they're familiar with these types of cases or if I should try the other options first given my tight deadline.

The Taxpayer Advocate Service handles all types of tax issues, including HSA distributions. They're especially helpful when you have a deadline approaching and haven't been able to resolve the issue through normal IRS channels. When I used them for my HSA issue, they were very familiar with the documentation requirements and actually helped me understand exactly what I needed to prove qualified medical expenses. The key with your tight deadline is to call them immediately and emphasize the urgency. They can often place a hold on your account while your case is being reviewed.

I tried this approach last year. Just a heads up that appointments at local IRS offices are often booked out weeks in advance. With only 2 days left, this probably won't work unless you get super lucky with a cancellation.

Thanks for this - my settlement does break down different amounts. About $21k was compensatory for financial losses and about $7k was listed as "other damages." Is there a way to deduct at least the compensatory part?

Based on your breakdown, if the $21k compensatory damages were related to financial losses from a business activity or investment property, then yes, that portion would likely be deductible in the appropriate section (Schedule C for business, Schedule E for rental property, etc.). The $7k listed as "other damages" is more ambiguous and would depend on the specific nature of those damages. If they're punitive damages, those typically aren't deductible. If they're for emotional distress without physical injury, those generally aren't deductible either. But if they relate to a business loss in some way, they might be.

Do cancelled checks count as proof or do you need more than that? I paid my settlement in 3 installments and have the cancelled checks but wondering if I need more documentation.

Do you need receipts for absolutely everything? I haven't been great about keeping track so far. Also, how do you calculate the portion of internet/phone to deduct?

Yes, you should keep receipts for everything - the IRS can ask for documentation if you're ever audited. But if you've lost some, bank/credit card statements can sometimes work as backup. For internet/phone, you need to determine what percentage is used for business. For example, if you estimate 30% of your phone use is for business communications with customers, you can deduct 30% of your phone bill. Just be honest and reasonable with your estimates. Some people keep a log for a few weeks to establish a usage pattern. Same concept applies to your home office - you calculate what percentage of your home's square footage is used exclusively for business, then deduct that percentage of rent/mortgage, utilities, etc.

Omg this tax stuff is so complicated. Im making bracelets and selling them on etsy too and i had no idea about any of this!!! How do you even make quarterly payments? And what's this 199A thing?

I thought you can't day trade in an IRA because of the limited deposits each year and trading restrictions?

You're right that there are limitations. IRAs have annual contribution limits ($7,000 for 2025 if you're under 50), and you can't use margin or do certain types of options trading. But you absolutely can do active trading within those limitations. Just no pattern day trading using margin, which requires $25,000 minimum equity in regular accounts. Some brokerages also have additional restrictions on IRAs, but the tax benefits can be huge for the trading you can do in there.

Thanks for the suggestion. I actually started doing this after I got confused about the tax implications. Do you happen to have a template you could share? I'm tracking basic info like buy/sell prices and dates, but wonder if I'm missing anything important for tax purposes.

Do you have a template for this coversheet you could share? I'm trying to visualize what should be on it besides just a list of documents.

I don't have a specific template, but I include these sections: Personal Info (names, SSNs, address), Income Documents (list all W-2s, 1099s by source), Deduction Documentation (charitable contributions, home office, etc.), Credits (child tax credit info), Estimated Tax Payments (dates and amounts), and Questions (things I specifically want the CPA to address). I also add a section for "Changes from Last Year" that highlights anything new (like your new baby) so they immediately know what's different.

Smart! What app do you use for this? Just regular notes app or something specific for tracking expenses?