I'm dealing with a similar situation with my vacation rental and this thread has been incredibly helpful! Based on what I'm reading, it sounds like the key is first determining whether your property falls under the 7-day rule (making it a business activity) or if it's a traditional rental activity. For traditional rental activities with longer average stays, the active vs passive participation distinction matters a lot for the $25,000 loss allowance. But for short-term rentals with average stays of 7 days or less, you're looking at material participation tests instead since it's considered a business activity. One question I still have - if you have multiple short-term rental properties, do you evaluate the participation tests for each property individually, or can you combine your activities across all properties? I manage three different Airbnb units and I'm not sure if my management time gets pooled together or evaluated separately for each property.

This is such a helpful discussion! I'm in a similar boat with my mountain cabin rental and the distinction between active vs passive participation has been driving me nuts too. What really helped me was tracking all my management activities in detail - even the time spent reviewing financial reports, approving repairs, and communicating with the property management company. I realized I was doing way more "active participation" work than I initially thought. One thing I learned the hard way is that the average rental period calculation is crucial. My cabin has some week-long rentals mixed with weekend stays, so I had to carefully calculate the average to determine if the 7-day rule applied. It turned out my average was 8 days, so I stayed in the traditional rental activity category where active participation mattered for the $25k loss allowance. The income phase-out is also something to watch carefully - if you're close to that $100k-$150k range, it might be worth timing some income or deductions to maximize your rental loss deduction eligibility.

Don't stress too much about this! You're actually in a better position than many people because you kept track of your mileage - that's going to save you a lot of money. With $4,800 in income and 3,600 miles of deductions at 65.5 cents per mile, you're looking at about $2,358 in deductions, which brings your taxable income down to around $2,442. The self-employment tax on that would be about $374 (15.3%), plus minimal income tax since you're in a low bracket. Even with penalties, you're probably looking at less than $600 total. File as soon as possible to stop the penalties from growing - you can use the regular 2023 tax forms (1040, Schedule C, Schedule SE) and most tax software will still let you e-file for 2023. Since this is your first time missing a filing deadline, definitely look into first-time penalty abatement when you talk to the IRS. Many people qualify for this and it can reduce or eliminate failure-to-file penalties. You've got this!

I went through almost the exact same thing with my Instacart deliveries from 2023! Made about $5,200 and completely missed filing because I was confused about the $600 threshold too. The stress was eating me alive until I finally dealt with it last month. Here's what I learned that might help you: First, you're actually in good shape with that mileage tracking - that's going to be your biggest deduction. Second, the IRS is surprisingly reasonable about first-time mistakes, especially when you're young and new to gig work. I ended up owing about $450 total after all deductions and penalties, which was way less scary than I thought. The key is filing ASAP to stop those penalties from growing. I used FreeTaxUSA to file my late 2023 return - it was like $15 and walked me through everything including Schedule C and SE. One thing that really helped my anxiety was calling the IRS directly after I filed to set up a payment plan. Yeah, the hold times suck, but once I got through, the agent was actually really helpful and not judgmental at all. They even mentioned the first-time penalty abatement without me asking about it. You've got this! It's not as bad as your brain is making it out to be.

Just want to make sure the OP and others understand capital gains taxes for 2025 filing. If you hold your investments for more than a year before selling (long-term capital gains), you get a much better tax rate (0%, 15%, or 20% depending on your income) than short-term gains (taxed as ordinary income). Making this distinction could literally save you thousands on your tax bill! I learned this the hard way when I day-traded some stocks and got hit with ordinary income rates on everything.

Great advice from everyone here! Just want to add one more consideration for @Ava Kim - since you're working at Target and trading stocks, you might want to look into tax-loss harvesting if you have any losing positions. You can sell losing stocks to offset your capital gains, which reduces your overall tax liability. For example, if you made $30k in gains but also have $10k in unrealized losses, you could sell those losing positions to bring your taxable gains down to $20k. You can even carry forward losses beyond your gains (up to $3k per year against ordinary income). This strategy works best when combined with the estimated payment approaches others mentioned. Just make sure to avoid the wash sale rule - don't buy back the same or "substantially identical" securities within 30 days of selling for a loss, or the IRS will disallow the loss deduction.

Don't forget about the primary residence exclusion! If this was your brother's primary residence for at least 2 of the 5 years before the sale, he might qualify to exclude up to $250,000 of gain from his income (or $500,000 if married filing jointly). Based on what you described, he lived there for about 2 years before moving out 2 years ago, so he might just barely qualify if the timing works out exactly. This could potentially eliminate any tax liability from the sale, even if he has to report it.

This is definitely a tricky situation that requires careful documentation. From what you've described, your brother needs to report the sale even though he didn't receive proceeds from the actual sale, because he was still legally on the deed. The key is treating this as a two-part transaction: (1) the original buyout he received when they split up, and (2) the formal sale that just happened. On Schedule D, he should report the sale with his cost basis being the original purchase price plus improvements, and his proceeds being only the buyout amount he received years ago (not the recent sale proceeds). You'll definitely want to include a detailed explanation with the return describing the situation. Also, try to get documentation of the original buyout agreement if possible - this will support your position if the IRS has questions. One important thing to check: make sure you understand whether he received a 1099-S form. If he did, the IRS will be expecting to see this sale reported. If the ex-girlfriend also reports part of the sale, you want to make sure there's no double-reporting of the same income.

Just adding that besides SSNs, there are other types of TINs too: - EIN (Employer Identification Number) for businesses - ITIN (Individual Taxpayer Identification Number) for non-citizens - PTIN (Preparer Tax Identification Number) for tax preparers - ATIN (Adoption Taxpayer Identification Number) for pending adoptions So while most people's TIN is just their SSN, not everyone's is!

Yes, you can definitely have multiple TINs! As an individual with a business, you'd have your SSN for personal tax matters and an EIN for your business. Many people have both - your SSN identifies you as an individual taxpayer, while your EIN identifies your business entity. You'll use your SSN on your personal tax return (Form 1040) and your EIN for business-related forms and transactions. Just make sure to use the correct number for the right purpose - SSN for personal stuff, EIN for business stuff.