Thank you for sharing this. Do you know if VITA sites can handle more complicated situations like mine with a decade of unfiled returns and mixed income types? I'm worried they might turn me away because it's too complex.

VITA sites can definitely handle your situation. They're staffed by IRS-certified volunteers who specifically help people with lower incomes navigate tax issues. Many locations have volunteers who specialize in self-employment and 1099 income situations. You're right that some VITA sites might initially seem hesitant about handling 10 years of unfiled returns all at once. What I'd suggest is going in first to get help determining which years you actually need to file for (likely not all 10), and then working on 2-3 years at a time. Most people in your situation find they only need to file 6 years back to get into compliance.

I filed 4 years of back taxes using FreeTaxUSA last year. You have to buy previous year versions separately, but it was WAY cheaper than TurboTax or H&R Block. I think I paid about $15 per year for state filing (federal was free). The downside is you have to print and mail the previous years - can't e-file them. Current year can be e-filed though.

Thanks for the tip on FreeTaxUSA! Did you have to wait for each year to process before filing the next one, or did you send them all at once? I'm worried about penalties accumulating while I'm getting everything organized.

That should be illegal though, right? They can't advertise a guarantee prominently and then hide in fine print that it doesn't apply to their main product that most people use?

I used it this year! It's definitely more basic than TurboTax but gets the job done. The interface isn't as polished but I saved like $120 and my refund was exactly the same as what TurboTax calculated when I did a comparison before submitting. Only downside is they don't support some more complex tax situations like multi-state filing or foreign income.

Thanks for pointing that out about the two-year limit! I think I got the year wrong in my original post - stepdad actually passed in 2021, not 2022, so this would indeed be the final year mom could use QSS status. My brother's income is definitely over that $4,700 threshold - he works part-time and makes around $18,000. Sounds like that automatically disqualifies him as a "qualifying person" for mom's QSS status then? So she'll have to file as single?

Yes, if your brother's income is around $18,000, that unfortunately means he cannot be considered a qualifying relative for tax purposes, regardless of how much support your mom provides. The gross income test is a firm threshold. Since he can't be a qualifying person for QSS purposes, your mom will need to file as Single for her 2023 tax return. For 2024 and beyond, she'll continue filing as Single unless her circumstances change (like remarriage).

This is actually a really good point - a lot of people don't realize there's still hope for HoH status! I work at a tax prep office and see this misconception all the time. One correction though - for Head of Household, if you're trying to qualify using a relative who isn't your child, that person MUST be your dependent. So the brother still needs to meet the qualifying relative tests including the gross income test.

Wait this sounds too good to be true. You're saying I can just deduct 20% of my income automatically? Does this apply to all 1099 work or only certain types? I do freelance programming.

Do you know which states offer these additional education credits? I'm in California and wondering if there's something similar I could claim.

I don't know all the states, but I know California doesn't have a specific education credit like New York does. Some states that definitely have education tax benefits include Indiana, Massachusetts, Michigan, and Wisconsin. The best way to find out is to check your state's department of revenue website or look at your state tax forms for education-related credits or deductions. Sometimes they're called different things like "Education Expense Credit" or "Tuition and Fees Deduction.

Thanks for the warning! Since I'm returning to college and have taken classes years ago, I'll need to figure out if I've already used up my 4 years of American Opportunity Credit eligibility. Is there any way to check that, or do I just need to look through my old tax returns?

You'll definitely want to check your previous returns if you have them. The AOC can only be claimed for 4 tax years total, and they don't have to be consecutive. If you went to college right after high school and claimed it then, you might have used it up already. If you don't have your old returns, you can get tax transcripts from the IRS website that will show if you claimed the credit before. Just go to IRS.gov and search for "Get Transcript." This is something you want to be 100% sure about because claiming it a 5th time would definitely trigger problems.