Just wondering - has anyone used those "tax relief" companies that advertise on radio/TV for situations like this? They claim they can settle with the IRS for "pennies on the dollar" but I'm not sure if they're legit or scams.

I've been through almost the exact same situation - 6 years of unfiled returns after getting overwhelmed by an initial IRS notice. The anxiety was paralyzing, but dealing with it was actually much less scary than I had built up in my head. Here's what worked for me: I started by requesting my wage and income transcripts online from the IRS website. This showed me exactly what employers had reported each year, so I didn't have to track down old W2s. Then I filed all the missing returns at once using tax software (TurboTax actually handles prior years pretty well). The biggest shock? I actually got refunds for 3 of those years because I had overpaid through withholdings. The refunds almost completely offset what I owed for the other years. Don't let the anxiety keep you frozen - the IRS genuinely wants to work with people who are trying to get compliant. You've been having taxes withheld this whole time, which shows good faith. Start with getting those transcripts and you'll have a much clearer picture of where you actually stand financially. You might be pleasantly surprised.

Has anyone used TurboTax for reporting crypto with all these fee adjustments? Their crypto section confused me last year.

I had the exact same confusion about bitcoin trading fees last year! After going through this myself, I can confirm what others have said - these fees definitely adjust your capital gains but aren't separate deductions. What really helped me was creating a simple spreadsheet to track everything. For each bitcoin sale, I had columns for: original purchase price, purchase fees, sale price, sale fees, and adjusted gain/loss. The formula was basically: (Sale Price - Sale Fees) - (Purchase Price + Purchase Fees) = Actual Gain/Loss. So for your $1,275 in fees, make sure you're adding purchase fees to your cost basis and subtracting sale fees from your proceeds before calculating gains. This will naturally reduce your taxable gains without needing to claim them as a separate deduction anywhere. Keep all your exchange statements showing these fees - the IRS loves documentation for crypto transactions. Good luck with your filing!

You mentioned a company car - was that during your contract work or only after becoming an employee? If you had it during contract work, there might be tax implications there too.

I went through something very similar last year - owing a big chunk because of mixed W-2 and 1099 income. The self-employment tax on that $13,500 is probably what's killing you the most. A few things that helped me: 1. Double-check if your employer reimbursements were incorrectly included in your 1099-NEC income 2. Even small business expenses add up - phone usage, internet, any equipment or supplies 3. Set up quarterly estimated payments for next year to avoid this mess again The underpayment penalty stings, but at least it's relatively small compared to your total bill. I'd definitely recommend seeing a tax pro - they often find deductions that save more than their fee costs. Don't beat yourself up too much, this is a super common situation when transitioning from contract to employee work.

Has anyone considered that exclusive use is sometimes not easy to prove? I use a room that's technically a bedroom as my home office, but it has absolutely nothing in it except office furniture and equipment. Would an IRS agent look at the room layout and decide it's not exclusive use just because it could be a bedroom?

One thing I haven't seen mentioned yet is the importance of tracking your actual work hours between locations. Since you mentioned going to the firm office every 2-3 weeks, you should document the time spent at each location throughout the year. The IRS uses this as a key factor in determining your "principal place of business." Keep a simple log showing dates, hours worked from home vs. firm office, and types of activities performed at each location. This becomes crucial evidence if you're ever audited. Since you're working 40+ hours weekly from home and only visiting the firm office occasionally, your documentation should clearly support that your home office is indeed your principal place of business. Also, make sure you're not mixing any personal activities in that dedicated room - no personal computer use, no storing personal items, etc. The exclusive use test is where many people trip up during audits.

Quick warning - don't forget to pay self-employment tax on your farm income! Schedule F income is subject to self-employment tax (15.3% covering both Social Security and Medicare). This catches a lot of new farmers by surprise.

Omar, your buddy gave you solid advice! As a newcomer to farm taxes myself, I was confused about this same thing last year. Schedule F business deductions are completely separate from your personal standard deduction - you get both! Think of it this way: your farm is a business entity, so those $3,800 in feed, equipment repairs, and seed costs are business expenses that get deducted on Schedule F. Meanwhile, you as an individual can still claim the standard deduction (or itemize if that's better) for your personal expenses. They don't interact with each other at all. Just make sure you keep detailed records of all your farm income and expenses, and that you're operating with genuine profit intent. The IRS wants to see that this is a real business, not just a hobby. Good luck with your farming venture!