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 hadn't even thought about state taxes or the LLC angle. Do you know if forming an LLC changes how depreciation works? And would I need to file a separate business tax return if I create an LLC?

A single-member LLC is typically treated as a "disregarded entity" for tax purposes, so you'd still report everything on your personal return using Schedule E. The depreciation works the same way regardless of whether you have an LLC or not. You generally don't need to file a separate business return for a single-member LLC used for rental property. However, if you elect to have your LLC taxed as an S-corp (which some people do to potentially save on self-employment taxes), then you would file a separate return. But for most small landlords with one property, keeping it simple with a disregarded LLC is usually the way to go.

I used TurboTax Premier last year for my rental and it worked fine. It walks you through all the Schedule E stuff and helps calculate depreciation. Just make sure you keep really good records of your expenses throughout the year. The one time I got confused, I used their live help feature and the tax expert cleared things up quickly.

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.

That's really good advice! Would you recommend asking them any specific questions to gauge their knowledge about medical deductions? I wouldn't even know how to tell if they're giving me good answers since I don't know much about this stuff myself.

Ask them specifically about the 7.5% AGI threshold for medical expenses and how they would help determine if you should itemize. A knowledgeable preparer will explain that medical expenses are only deductible for the amount exceeding 7.5% of your adjusted gross income, and they'll want to know if you have other potential deductions that could make itemizing worthwhile. You could also ask what types of medical expenses are deductible that people commonly miss. They should mention things like mileage to medical appointments, lodging while receiving medical care away from home, home modifications for medical purposes, or certain insurance premiums. If they only mention obvious things like doctor bills, they might not have specialized knowledge.

Thats true, my local HR Block has an enrolled agent who specializes in medical deductions. Shes way better than the seasonal people they hire and not much more expensive. I've used her for 3 years now.

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.