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.

Just a heads up, the penalties for not filing FBARs can be INSANE. Non-willful violations can be up to $12,921 per violation (for 2023), and willful violations can be the greater of $129,210 or 50% of the account balance at the time of violation. Don't mess around with this form!

This is really helpful information! I'm dealing with a similar situation where I have joint ownership of a foreign account with my spouse (we're both US citizens but the account is in the UK from when we lived there). Based on what Dylan explained, since I'm a joint owner, I definitely have financial interest and need to report it on the FBAR. One thing I'm still confused about though - do I need to report the full account balance or just my "share" as a joint owner? The account has about £18,000 but technically half of that is my spouse's money. Should I report the full balance or just £9,000?

Emma, I feel your pain! I was in the exact same boat last year - frantically searching for a 1099-SA while H&R Block held my tax return hostage. Here's what worked for me: First, check if you actually made any HSA withdrawals in 2024. If you only contributed to your HSA but never took money out for medical expenses, you won't have a 1099-SA. Sometimes tax software asks about forms you don't actually need based on how you answer other questions. If you did make withdrawals, your HSA provider is required to have the form available by January 31st. Try these steps in order: 1. Log into your HSA provider's website (check your paystub for the company name) 2. Look for "Tax Documents" or "Tax Forms" section 3. If you can't find it online, call the customer service number 4. Ask your HR department - they often have direct contacts Don't panic about owing taxes! The 1099-SA just reports withdrawals, but if you used the money for qualified medical expenses (prescriptions, doctor visits, etc.), those are tax-free. Worst case scenario, you can file for an extension to give yourself more time while still enjoying your trip. The stress isn't worth it - this happens to tons of people every year and it always gets sorted out! Good luck!

Emma, I completely understand your frustration! This exact situation happened to me two years ago and I was pulling my hair out trying to figure out what a 1099-SA even was. Here's the quick answer: The 1099-SA reports any money you withdrew from your Health Savings Account (HSA) during 2024. Since H&R Block is asking for it, you definitely made at least one withdrawal from your HSA last year. To find your form, check your most recent paystub first - it should show which company manages your HSA (like HealthEquity, Optum Bank, HSA Bank, etc.). Then go to that provider's website and log into your account. Look for a "Tax Documents" or "Forms" section - they're required to post these by January 31st. If you can't access it online, call the customer service number on your HSA debit card or any HSA statements you've received. They can usually email you a copy immediately. Here's the good news - having a 1099-SA doesn't automatically mean you owe more taxes! If you used the HSA money for qualified medical expenses (doctor visits, prescriptions, medical procedures), those withdrawals are completely tax-free. H&R Block will just ask you to specify which expenses were medical-related. Don't stress too much about this - it's super common and you should be able to get the form quickly once you contact your HSA provider. You'll definitely get your taxes done before your trip!

I wish the tax code wasn't so unnecessarily complicated!! Why can't points just be points and deductions just be deductions? My freind got audited over this exact issue and the IRS agent didn't even understand it. He kept changing his answer!!!!

This is exactly the kind of situation where documentation is everything. I went through something similar last year with an $820k mortgage and $8,200 in points. The key thing I learned is to keep meticulous records of exactly how much of your loan went toward the home purchase vs. any improvements. Since you mentioned $50k went to renovations, that could actually work in your favor. The IRS treats home improvement debt differently - it's not subject to the same $750k cap as acquisition debt. So you'd potentially have $780k subject to the limit (not the full $830k), which would increase your deductible percentage. My advice: get your closing statement, contractor receipts, and any other documentation organized now. When your tax person gets back, they'll be able to properly allocate the points between acquisition debt and improvement debt. This could save you several hundred dollars in additional deductions. Don't just assume you're limited to the simple ratio calculation - the improvement portion changes everything.

One thing I haven't seen mentioned yet is quarterly estimated tax payments. Since you're making "decent money" after 8 months, you'll likely need to make quarterly payments to avoid underpayment penalties. The IRS expects you to pay as you earn, not just at year-end. For 2025, if you expect to owe $1,000 or more in taxes on your golf business income, you should be making quarterly payments. The deadlines are January 15, April 15, June 16, and September 15. You can use Form 1040ES to calculate what you owe. Also consider opening a separate business checking account if you haven't already. It makes tracking so much easier and looks more professional if you ever get audited. You can deduct the monthly fees as a business expense too. Keep up the great work with the side business - sounds like you're really building something solid!

Great thread everyone! As someone who's been through the home business learning curve, I wanted to add a few practical tips that helped me stay organized: 1. **Monthly reconciliation** - Set aside time each month to categorize expenses and reconcile your business account. Don't wait until tax time! I use a simple spreadsheet with columns for date, vendor, amount, category, and business purpose. 2. **Photo documentation** - Take pictures of receipts immediately and store them in a cloud folder organized by month. I've saved myself multiple times when paper receipts faded or got lost. 3. **Business purpose notes** - For any expense that could be questioned (like those golf rounds for testing clubs), write the business purpose directly on the receipt or in your expense tracking. "Tested driver repair for Client X" is much better than trying to remember 6 months later. 4. **Mileage log app** - Use an app like MileIQ or even just the notes app on your phone to track business mileage in real-time. I tried keeping a paper log and failed miserably. The key is building these habits now while your business is growing. It's so much easier to maintain good records from the start than to reconstruct everything later. Sounds like you're already thinking about this stuff the right way - that puts you ahead of most new business owners!