Something nobody has mentioned yet - check if you can deduct it on your state taxes! Even if you can't benefit from itemizing on your federal return, some states have different rules or lower thresholds for medical expense deductions. For example, my state allows medical expense deductions that exceed just 4% of income instead of the federal 7.5%. Also, some states offer special credits for people with lower incomes who have high medical costs.

One thing to consider - are you eligible for the Earned Income Tax Credit (EITC)? With an income of $22k, you might qualify for a refundable credit that could be more valuable than trying to deduct the dental expenses. Also, if your income is actually $22k from employment and you paid for the dental procedure yourself, you might look into an HSA for future medical expenses if your employer offers one. Too late for the current expense, but helpful for the future.

Quick tip: If it's a public university, check their W-9 form which is often available on their procurement or vendor relations website. Almost all universities make their W-9 available online for vendors who need to pay them, and it has their EIN right at the top. Just google "[university name] W-9" and you'll probably find it in seconds. Saved me tons of headache when dealing with a similar situation for my continuing education courses.

Someone please correct me if I'm wrong but I think you might be eligible for the Lifetime Learning Credit even without the 1098-T? It's meant for exactly this type of continuing education and certificate programs. As long as you have proof you paid tuition to an eligible educational institution you should be able to claim it.

Something important that hasn't been mentioned: once approved for the Form 4361 exemption, you're permanently opting out of Social Security benefits based on those earnings! I've seen people file this form without realizing they're giving up retirement benefits. Also, the IRS is very strict about the timing. You must file by the due date of your tax return for the second year in which you had self-employment earnings of $400+ from ministerial services. Miss that window and you're permanently required to pay self-employment tax, no exceptions.

Just a heads up, the IRS is VERY specific about who qualifies as a "Christian Science practitioner" for Form 4361. You need to be listed in the Christian Science Journal as a practitioner or be a commissioned Christian Science reader. They will verify this! It's not just about attending services or being a member of the church.

If you can't wait to get the certified letter, you might want to check if your post office offers "informed delivery" which lets you see scanned images of your mail online. Might at least let you confirm if it's from the IRS before you panic too much. Also, if you're really tight on money, call the Taxpayer Advocate Service at 877-777-4778. They can sometimes intervene in hardship cases, especially if you're at risk of not being able to afford basic living expenses because of the tax debt. They're separate from regular IRS collections and can sometimes be more helpful.

One thing I learned when dealing with a tax lien - DON'T ignore that certified letter! The clock on your appeal rights starts ticking from when they ATTEMPT delivery, not when you actually get it. I think you have 30 days to request a Collection Due Process hearing, which can stop the lien while you work things out. Also, if you get the lien notice and then pay in full, make sure to specifically request a lien WITHDRAWAL not just a release. A release just shows it's paid but stays on your credit report, a withdrawal makes it like it never existed. Huge difference for your credit score!

One thing to consider - if you're filing back taxes and expect refunds, double check if you had any stimulus payments during those years. For 2021 especially, if you didn't receive the third stimulus payment ($1,400 per person), you might be eligible to claim the Recovery Rebate Credit on your return. Also, if you had children and were eligible for the expanded Child Tax Credit in 2021, make sure that's accounted for. Those were partially sent as advance payments, but you might be eligible for the remainder. Those two things alone could significantly increase your refund for 2021!

I just went through this whole process of filing 3 years of back taxes. My biggest piece of advice is to gather ALL your documents before starting. Make a checklist: - W-2s from all employers for each year - 1099s (interest, dividends, contractor work, etc) - Mortgage interest statements - Student loan interest - Health insurance forms - Any major life events (buying home, education, etc) Once you have everything organized by year, the software is actually pretty straightforward. I used TaxSlayer for all my back years and while it was a bit pricey (about $40 per year including state), their interface was really easy to use for someone who was overwhelmed like I was.