As someone who's been getting Robinhood 1099s for years now, my advice: look at page 1 or 2 for the summary section. It should have totals for short-term gains/losses, long-term gains/losses, dividends, and interest. Those are the big numbers that affect your taxes. Don't get lost in the transaction details unless you need to verify something specific.

One thing I learned the hard way with my first Robinhood 1099 - make sure to check if you have any state tax implications too! Some states don't tax capital gains at all, while others tax them as regular income. Also, if you made estimated tax payments during the year, don't forget to account for those when calculating what you might still owe. The federal tax estimate is just part of the picture. I ended up owing way less than I thought because I had forgotten about the quarterly payments I made through my business. Good luck with your first investment tax filing - it gets easier once you understand the format!

One thing nobody mentioned yet - if your brothers self-employment income is really small (like under $400 net profit) he doesn't have to pay self-employment tax on it, but still has to report the income. Saved me some $$$ when I was just starting my side gig!

Another important thing to consider is recordkeeping! For your brother's freelance work, he needs to track EVERYTHING - receipts, mileage, client payments, business equipment purchases, even home office expenses if he works from home. The IRS requires good documentation for all business deductions. I learned this the hard way when I couldn't find receipts during an audit. Now I use a simple spreadsheet or app to track expenses monthly rather than scrambling at tax time. For mixed-use expenses like his phone or internet, he'll need to calculate the business percentage based on actual usage. The key is being able to prove the business purpose if ever questioned. Also, since he has both W-2 and 1099 income, he should definitely consider making quarterly estimated tax payments for the freelance portion. The IRS expects you to pay taxes throughout the year, not just at filing time, and there can be penalties if you owe too much in April.

Has anyone used TurboTax to file with Real Estate Professional Status? I'm not sure if it handles this situation correctly and I don't want to mess it up.

Based on your numbers, you're unfortunately just short of qualifying for Real Estate Professional Status right now. With 850 hours on real estate activities, you easily meet the 750+ hour requirement. However, the "more than half your working time" test is where you fall short - your 1,500 consulting hours plus 850 real estate hours means real estate is only about 36% of your total working time. A few potential strategies to consider: 1. Could you reduce your consulting to part-time (maybe 20-25 hours/week) while maintaining income through higher rates? 2. Are there additional real estate activities you're not tracking? Time spent researching markets, attending real estate education courses, or networking with other investors all count toward your hours. 3. Consider whether some of your current activities could be reclassified - for example, time spent learning about tax strategies for rental properties counts as real estate professional time. The good news is you're not that far off. If you could shift the balance to where real estate represents 51%+ of your working time, you'd qualify and could deduct that $18,500 loss against your consulting income. Given the potential tax savings, it might be worth running the numbers to see if reducing consulting hours could actually increase your after-tax income overall.

This is such a common mistake with teenage filers! I went through the exact same thing with my daughter two years ago. The good news is that it's totally fixable, though it requires some patience. From my experience, you have three realistic options: 1. **Wait for your son to file Form 1040X** - This is the "correct" way but takes 8-16 weeks to process. Your son would amend his return to indicate he can be claimed as a dependent. 2. **File your return without claiming him this year** - You'll get a smaller refund now, but you can file your own 1040X later to claim him once his amendment processes (adding even more waiting time). 3. **File for an extension** - Gives you until October to file, but delays your refund. Honestly, if you need the refund money soon, option 2 might be your best bet despite the hassle. You'll at least get some money now rather than waiting months for the full amount. One tip: Make sure your son understands the dependency rules for next year! The software questions can be confusing, but if he's still in high school and you're supporting him, you should be claiming him. Good luck!

I just went through this exact situation last month! My 16-year-old made the same mistake with his first W-2 job. Here's what I learned from calling the IRS directly: The fastest resolution is actually to have your son file Form 1040X (amended return) to correct his filing status. While everyone says it takes 8-16 weeks, mine was processed in about 6 weeks. The key is to clearly write in the explanation section: "Correcting dependency status - should be claimed as dependent by parent." In the meantime, you can go ahead and e-file your return claiming him. The IRS systems will initially reject it, but once your son's amendment processes, you can resubmit your return. This avoids you having to file your own amendment later. Pro tip: Include a cover letter with your son's 1040X explaining the situation. The IRS agent told me this helps speed up processing because it's immediately clear what the issue is rather than them having to figure it out. Don't stress too much - this happens constantly with teenage filers. The IRS sees these dependency mix-ups all the time and they have a pretty streamlined process for fixing them!

One mistake I see a lot - make sure your properties actually qualify as short-term rentals for tax purposes. Its not just about being on Airbnb. The average stay needs to be less than 7 days, and you need to be providing substantial services (similar to hotels). Also remember that material participation for each property is determined separately unless you make a grouping election. If your spending 600 hours combined across all properties, but only 150 on one of them, that specific property might not qualify as active without proper grouping.

Great question about the 7-day average and substantial services! The IRS looks at several factors to determine if you're providing "substantial services" similar to a hotel: - Daily housekeeping or frequent cleaning (you've got this covered) - Providing linens, towels, and toiletries (check) - Concierge-type services like local recommendations, booking activities - Maintenance and repair services - Guest communication and problem resolution Based on what you mentioned (linens, toiletries, coffee, cleaning between guests), you're likely meeting the substantial services test. The key is that these services are provided for the convenience of the occupant, not just basic property maintenance. For the material participation piece that Laura mentioned - you're absolutely right about the grouping election. With 600-700 total hours across multiple properties, Ethan should definitely consider making an election to group his rental activities together. This allows him to meet the material participation test for the entire grouped activity rather than each property individually. The election needs to be made by filing a statement with your tax return, and once made, it's generally binding for future years unless there's a material change in circumstances.