I went through something similar last year with about $8k in back taxes from some 1099 work. After doing a ton of research, I ended up handling it myself and it was way easier than I expected. The key thing is to not panic - the IRS actually wants to work with you if you're proactive. I called their main number early in the morning (around 7 AM when they opened) and got through in about 45 minutes. The agent was actually really helpful and walked me through setting up a 60-month payment plan. One thing I learned is that you can request "first-time penalty abatement" if you've been compliant in previous years. This can wipe out a big chunk of the penalties (not the actual tax owed, but the penalty fees). For me, this saved about $1,200. My advice: try the DIY route first. If you get stuck or overwhelmed, then consider getting help. But for a straightforward situation like yours, you can probably handle it yourself and save thousands in fees.

I went through a very similar situation about 18 months ago - owed around $14k from some consulting work where I messed up the quarterly payments. The stress and panic you're feeling is totally normal, but honestly the IRS is much more reasonable than those scary letters make it seem. I initially got quotes from three different tax resolution companies and they ranged from $3,500 to $6,200 just for their fees. One place literally told me they could "probably" get my debt reduced to $2,000 but couldn't guarantee anything. When I pressed them on specifics, it became clear they were just going to submit the same forms I could do myself. Instead, I ended up going the DIY route and it saved me thousands. Set up a 72-month payment plan directly through the IRS website for about $205/month. The whole process took maybe 30 minutes online, and I didn't have to deal with any pushy salespeople or worry about getting scammed. The reality is that for most people with straightforward tax debt like yours, those expensive services just aren't worth it. The IRS has gotten much better about working with taxpayers who are proactive about resolving their debt. Save your money and try handling it yourself first!

If ur making under $5000 dont even bother filing tbh. I didnt file for 3 years when I was doing odd jobs and nothing happened. The IRS doesnt care about small amounts.

As someone who went through this exact same situation when I was 20, I want to emphasize a few key points that might help you feel more confident about the process: First, don't stress too much about perfect record-keeping for this past year - the IRS understands that many people doing casual work don't have pristine records. Make your best good-faith estimate of your total income and document how you arrived at that number. For your Schedule C, you can deduct reasonable business expenses even without perfect receipts - things like tennis balls, equipment, gas money for traveling to lessons, etc. Just be reasonable and honest. Going forward, definitely set up better tracking. I use a simple spreadsheet with columns for date, student name, amount, and method of payment. Takes 30 seconds per lesson and saves hours during tax season. One thing I wish someone had told me: even though you'll owe self-employment tax (about 15.3% on your net profit), you'll likely get most or all of your income tax back due to the standard deduction. So don't panic about owing huge amounts. The Roth IRA is absolutely worth it at your age - compound growth over 40+ years is incredible. You're making a really smart financial decision here!

Has anyone used TurboTax or H&R Block for filing US taxes from Canada? I'm wondering if the regular versions work or if I need something special for expat taxes.

I was in a very similar situation a few years ago - US citizen living in the UK with no income for several years due to health issues. The anxiety about being "in trouble" with the IRS was really overwhelming! Here's what I learned: Yes, technically you should file even with zero income, but the IRS is generally understanding about people who genuinely didn't know about the requirement, especially when no taxes are owed. The key is getting compliant going forward. Since you have no income, you likely qualify for the Streamlined Filing Compliance Procedures, which is designed for people in exactly your situation. You'll need to file the last 3 years of tax returns (even if showing zero income) and 6 years of FBARs if you have Canadian bank accounts over $10k. The good news is that with zero income, you won't owe any taxes or penalties. I'd recommend getting professional help just to make sure everything is filed correctly and to give you peace of mind. Don't let the anxiety eat at you - this is much more common than you think and very fixable!

I went through this exact process last year when I acquired a Delaware LLC from overseas. Here's what worked for me: 1. **ITIN Application First** - As others mentioned, you absolutely need an ITIN before you can complete Form 8822-B. I used Form W-7 and included a letter explaining my need for the ITIN as the new responsible party of a US business entity. 2. **Documentation Tips** - Make sure you include certified copies (not originals) of your passport and any other identity documents. I also included a copy of the business purchase agreement to prove my legitimate need for the ITIN. 3. **Timeline** - My ITIN took about 9 weeks to arrive. Once I had it, the 8822-B processing was much faster - about 3 weeks. 4. **Pro Tip** - Consider mailing your W-7 application via certified mail so you have proof of delivery. The IRS processing centers can be slow to acknowledge receipt. The whole process took about 3-4 months total, but it's really the only proper way to handle this situation. Don't try to shortcut it by submitting incomplete forms - you'll just create more delays and complications down the road. Good luck with your acquisition!

I went through this exact situation 6 months ago when I purchased a tech startup from California. The process definitely requires patience, but here's what I learned that might help speed things up: **ITIN Application Strategy:** - Submit your W-7 with a comprehensive business justification letter - Include copies of your business acquisition documents (purchase agreement, operating agreement, etc.) - Attach a projected tax return showing estimated business income to strengthen your case for needing an ITIN **Critical Timing Tip:** Don't wait for your ITIN to arrive before preparing your 8822-B. You can fill out everything except the ITIN field, so when your number arrives, you can immediately submit the form. This saved me about 2 weeks. **Follow-up Strategy:** Around week 6 of your W-7 processing, start calling the IRS International line (267-941-1000) weekly to check status. They can often tell you if additional documentation is needed before you receive a formal notice. The entire process took me about 11 weeks total, but the business was fully transferred without any compliance issues. It's definitely worth doing properly rather than trying workarounds that could create problems later. One last note - make sure your business continues filing any required returns during this transition period using the existing responsible party information until the change is officially processed.

Don't forget to consider state taxes too! The federal exclusion is great, but some states have different rules for capital gains on home sales. Where are you located? Some states follow the federal guidelines, but others have their own quirky rules.

I'm so sorry for your loss, Justin. Dealing with tax implications while grieving is incredibly difficult. One additional thing to keep in mind as you navigate this process - make sure you have all the necessary documentation organized before you sell. Beyond what others have mentioned about cost basis and improvements, you'll want to have your wife's death certificate readily available, proof that the home was your primary residence for at least 2 of the last 5 years, and documentation of any major improvements you've made. Since you're in Colorado and within the 2-year window, it sounds like you're in a good position to take advantage of the full $500K exclusion. Given the complexity of your situation and the significant amount of money involved, I'd strongly recommend consulting with a tax professional who has experience with widower exclusions before you finalize the sale. They can help ensure you're maximizing all available benefits and properly documenting everything for when you file. Take care of yourself during this difficult time.