14 Don't overthink this too much! I've been selling art at shows for years. I use my brand name on my W-9, but I've never formally registered it. The main thing is that you report all your income on your taxes. If you're a sole proprietor, it all goes on your Schedule C anyway.

Great discussion here! As someone who just went through this process myself, I'd recommend checking your state's specific DBA requirements before making any decisions. In my state, using a business name without registration is fine for tax purposes, but I ran into issues when trying to open a separate business bank account later. One thing that really helped me was creating a simple spreadsheet to track all my art-related income and expenses from day one, regardless of what name I use on forms. This makes tax time much easier whether you're operating under your legal name or a brand name. Also, don't forget that even if you use a DBA on your W-9, you'll still need to use your legal name and SSN as the primary taxpayer information. The business name is just additional identification for their records.

Has anyone here back filed with just the 1040 forms from the IRS website? Or do you really need to use tax software for each specific year? Im trying to save money and wondering if I can just download the forms for each year and fill them out myself.

Just wanted to add something that might help - when you're gathering documents for back filing, make sure to check if you have any 1099s you might have forgotten about. I missed a 1099-INT from a savings account that only had like $12 in interest, but it still needed to be reported. Also, if you can't locate all your documents, you can request wage and income transcripts from the IRS for free through their website or by calling. These transcripts show what income documents were filed under your SSN for each year, which can help you identify any missing paperwork. The good news is that most people in your situation end up getting refunds for the years they didn't file, especially if you had taxes withheld from your paychecks. So don't stress too much - you're likely going to be pleasantly surprised once you get everything sorted out!

One thing to keep in mind: American Opportunity Credit can only be claimed for 4 tax years, so if you've already claimed it for 4 years, you might need to look at the Lifetime Learning Credit instead. Also, do you have any documentation showing you were enrolled in 2023 and that you paid in 2022? You'll want to keep those records (enrollment verification, payment receipts, etc.) in case you're audited, especially if you're claiming the credit without having a 1098-T for that specific year.

Pro tip: If you file an amended return to claim education credits, make sure you're specific about which semester the expenses were for! I made this mistake - claimed Spring 2023 expenses on my 2022 return (correctly, since I paid in Dec 2022) but didn't clearly document which semester it was for. Ended up getting flagged for review because it looked like I was claiming the same semester twice.

Anyone have advice on the best apps to track expenses for contractors? I'm terrible at keeping receipts and always scrambling at tax time.

This is such great advice in this thread! As someone who just transitioned from W-2 to contractor work, I had the same panic about taxes. One thing I wish I'd known earlier - you can also make your quarterly payments online through the IRS Direct Pay system (https://www.irs.gov/payments/direct-pay) which is free and way easier than mailing checks. Also, if you're just starting out and unsure about your income projections, you can use the "safe harbor" rule - pay 100% of last year's tax liability (or 110% if your prior year AGI was over $150k) spread across four quarterly payments, and you won't get hit with underpayment penalties even if you end up owing more at filing time. This takes a lot of the guesswork out of those first few quarters while you figure out your actual tax situation.

Does anyone know if it matters that the land is undeveloped? I inherited a vacant lot from my dad in 2019 and haven't done anything with it. Does the stepped-up basis rule still apply the same way?

Brandon, congratulations on holding onto that land for 20 years - that's quite an investment! You're absolutely right about the stepped-up basis for inherited property. As others have mentioned, your cost basis would be the $60,000 fair market value when you inherited it in 2005, not your grandfather's original $8,000 purchase price. One thing I'd add is that you might want to double-check if there were any estate taxes paid on the property when your grandfather passed. Sometimes the estate tax return (Form 706) can provide additional documentation of the property's value at the time of death, which could be helpful for your records. Also, since you've held it for 20 years, you'll definitely qualify for long-term capital gains rates. Depending on your income level, you could pay 0%, 15%, or 20% on the $127,000 gain (assuming that $60,000 basis is accurate). If you're in a lower income bracket, you might even qualify for the 0% rate on some or all of the gain. Just make sure to keep good records of whatever documentation you use to establish that 2005 value - county assessments, comparable sales, or any appraisals from that time period. The IRS may want to see supporting evidence if they ever question the basis.