That's super helpful! I didn't realize I could estimate and amend later. I do have most of my insurance EOBs and could probably get the pharmacy summaries easily. Would bank statements showing payments to medical providers be acceptable if I can't get the detailed receipts?

Bank statements can be supporting documentation, but they're not ideal on their own since they don't show what the payment was specifically for. The IRS wants to know that the expenses were medically necessary and not for something like cosmetic procedures. Your best approach is to use the EOBs from your insurance company - they typically show both what was covered and what you paid out of pocket. Most insurance providers have online portals where you can download a full year's worth of statements. Also contact your pharmacies for medication summaries, which they can usually provide immediately. Between those two sources, you might account for 80-90% of your expenses without much hassle.

I second this! I have a chronic condition too and didn't realize I could deduct all the travel to specialists (400 miles round trip several times a year). Also deducted my CPAP supplies, air filter for allergies (with doctor's note), and even the portion of my utilities for the medical equipment. Added about $3k to my deduction!

Can you explain this with an example? I'm not sure I understand how the math works out.

Sure! Let's say you bought stock for $1,000 several years ago, and now it's worth $2,500. If you sold it, you'd pay capital gains tax on the $1,500 profit - which might be $225 if you're in the 15% capital gains bracket. Instead, if you donate that stock directly to charity, two things happen: First, you get a deduction for the full $2,500 current value (if you itemize). Second, you completely avoid paying the $225 in capital gains tax you would have owed if you sold it. So compared to selling the stock and donating cash, you save an extra $225 in taxes.

Unfortunately, that special provision expired. During the pandemic, the CARES Act allowed people to deduct up to $300 ($600 for married couples) in charitable donations without itemizing. But that was temporary and is no longer available for current tax years. For 2025, you'll need to itemize deductions to get any tax benefit from charitable giving. That said, it's always worth checking for new tax laws as we get closer to filing season, as Congress occasionally introduces new provisions.

Good point! I work for an insurance company (not giving official advice here) but generally we want the insurance policy to be in the name of the person who has "insurable interest" - which is usually the titled owner. But there are options like adding the driver as a regular operator or sometimes having a non-owner policy.

Where do you find old returns in FreeTaxUSA? I've been using them for years but never figured out how to see my past filings.

You need to log into your FreeTaxUSA account, and on the main dashboard there should be a section called "Prior Year Returns" or "Tax Return History." Click on that and you'll see all the years you've filed with them. Select 2019, and you can view or download the full PDF of that return. If you downloaded and saved your returns each year, you can also just open the PDF directly from your computer. The Schedule A is usually around page 11-13 of the complete return.

States are required to issue 1099-Gs for all refunds they send, but sometimes they don't if the amount is very small. $340 is actually right around the threshold where some states might not bother. Technically you're still supposed to report it if you itemized that year, but realistically the tax impact would be very minimal.

I didn't even think about that! Do I need to be making quarterly payments on freelance income going forward? How do I figure out how much to pay?

Yes, if you expect to owe $1,000 or more in taxes at filing time, you should be making quarterly estimated payments. The easiest way to calculate is to take about 30% of your freelance income (that covers both income tax and self-employment tax for most people) and pay that amount quarterly. You can make these payments online through the IRS Direct Pay system or through the EFTPS (Electronic Federal Tax Payment System). There's also Form 1040-ES which has worksheets to calculate a more precise amount if you want to be more accurate. Setting aside money from each freelance payment into a separate savings account specifically for taxes is also a good habit to start.

This is super important! I once amended my federal return but forgot to do my state amendment. Ended up getting a notice with penalties a year later. Each state has different forms for amendments - some call it a "corrected return" instead.