Just want to add another perspective here - I've been dealing with roommate rental income for about 3 years now and learned some things the hard way. One thing that caught me off guard initially was keeping track of improvements vs. repairs. If you fix something that was already broken (like a leaky faucet), that's a deductible repair expense. But if you upgrade something (like replacing old carpet with new hardwood), that's an improvement that has to be depreciated over time instead of deducted immediately. Also, definitely keep receipts for EVERYTHING. I got lazy about it my first year and regretted it when tax time came around. Even small things like furnace filters or light bulbs can add up to meaningful deductions when you're calculating the rental portion. A simple spreadsheet or even just a shoebox works - just make sure you're documenting all your housing-related expenses throughout the year. The percentage calculation Logan mentioned is key too. I calculate mine based on square footage of bedrooms plus shared common areas. So if my roommates have 3 out of 4 bedrooms and we all share the kitchen/living room equally, I use about 62.5% for my rental portion calculations.

Great question! I went through this exact situation when I first bought my house. Yes, you absolutely need to report all $1,950/month ($650 x 3) as rental income on Schedule E, even though it's going toward your mortgage. Here's what helped me get organized: First, figure out what percentage of your home the roommates are using. If they each have their own bedroom and you all share common areas equally, you might calculate it as (3 bedrooms ÷ 4 total bedrooms) + (shared spaces ÷ 4) for your rental percentage. You can then deduct that same percentage of expenses like: - Mortgage interest (not the principal payments though!) - Property taxes - Homeowners insurance - Utilities (if you pay them) - Repairs and maintenance - Depreciation on the rental portion Keep really detailed records from the start - trust me on this. I use a simple Excel sheet to track every house-related expense throughout the year. Even small things like air fresheners or toilet paper can add up when you're calculating your rental portion deductions. The key thing to remember is that while you have to report the income, the deductions will likely offset most or all of it, especially in your first year when you can claim depreciation. Just make sure you're working with the right tax software (you'll need one that handles Schedule E) or consider talking to a tax professional for your first year to make sure you're doing everything correctly.

One thing nobody mentioned - make sure you're tracking your deadhead miles too (the miles driving back from a delivery when you don't have food in the car). Those miles are fully deductible for your DoorDash work! I made the mistake of only counting miles when I had food in the car my first year and missed out on almost 40% of my potential deduction. For your 1099 work, it's any mile driven for business purposes, including getting back to a hotspot area.

I'm a newer delivery driver and this whole thread has been incredibly helpful! I had no idea about the W-2 vs 1099 distinction for mileage deductions. I've been driving for a local pizza place (W-2) for about 6 months and just started with Uber Eats on weekends. Reading through everyone's experiences, it sounds like I need to completely separate my tracking - no deductions for the pizza place miles, but full business mileage deduction for Uber Eats including those return trips I never thought to track. One question though - if I'm doing both jobs in the same shift (like finishing my pizza place shift then immediately going online for Uber Eats), how do I handle the transition? Is the drive from the pizza place to my first Uber pickup considered business mileage for the 1099 work? Also want to echo what others said about asking for higher reimbursement from employers. My pizza place only pays 40 cents per mile and after reading Connor's success story, I'm definitely going to have that conversation with my manager!

This is such a helpful thread! I'm in a similar situation with a property in the Philippines that I inherited from my parents about 8 years ago. I've been renting it out and reporting the income, but I'm considering selling it now. One thing I'm curious about - since this was inherited property, do I use the fair market value at the time of inheritance as my basis, or do I need to go back to what my parents originally paid for it decades ago? And if it's the fair market value at inheritance, which exchange rate do I use - the one from when they passed away or from when the property was officially transferred to me (which took about 6 months due to probate)? Also, has anyone dealt with the situation where the foreign country requires you to pay their capital gains tax before you can transfer the proceeds out of the country? I'm wondering how that affects the timing of when I need to report everything to the IRS.

This is such a valuable discussion! I'm dealing with a similar situation with property in Germany that I bought in 2008. One thing I'd add that hasn't been mentioned yet - make sure you keep detailed records of any improvements or renovations you made to the property over the years. These can be added to your basis and reduce your capital gains. Also, if you've been depreciating the property on your US returns, remember that you'll need to use the depreciation amounts you actually claimed (or were allowed to claim, whichever is greater) when calculating the depreciation recapture, not necessarily what you should have claimed. For anyone dealing with properties in EU countries, be aware that some countries have withholding requirements where they'll hold back a percentage of the sale proceeds to cover potential tax liabilities. You can usually get this refunded later, but it affects your cash flow timing. Germany withheld about 25% of my sale proceeds and it took 8 months to get the refund after filing their tax return. The currency exchange impact is real - in my case, the Euro had strengthened against the dollar since 2008, so even though the property only appreciated modestly in Euro terms, my dollar-based capital gain was much larger than expected.

Quick question about this whole 1099-NEC situation - does it make more sense to use TurboTax or H&R Block when you have one of these forms? I'm in the same boat but haven't started my taxes yet.

Hey! I went through this exact situation with my education internship last year. The fact that you received a 1099-NEC means you're considered an independent contractor for tax purposes, even though it was an internship for college credit. This is actually pretty common with paid educational placements. A few key things to know: - Yes, you'll need to file Schedule C and pay self-employment tax (about 15.3% on your net earnings) - BUT you can deduct legitimate business expenses like mileage to/from the school, any supplies you bought for the classroom, etc. - Keep good records of any expenses related to this work For the financial aid question - this income will count toward your AGI, which could potentially affect your FAFSA calculations for next year, but $2,800 likely won't have a huge impact. Since you're already using FreeTaxUSA, they have good guidance for Schedule C. Just make sure to answer "yes" when they ask if you're self-employed (even though it feels weird!) and enter your teaching assistant work as your "business." The good news is this is totally manageable, and lots of students deal with this same situation. You've got this!

Don't forget to check if you qualify for Earned Income Tax Credit even with unemployment income! My combined income from work + unemployment last year was around $32k and I still qualified for a decent EITC. It significantly reduced what I owed on my unemployment benefits. Most tax software will check this automatically, but just wanted to mention it since it made a huge difference for me.

I went through almost the exact same situation in 2023! Got laid off, collected unemployment for 7 months, and completely forgot about the tax implications until it was time to file. Here's what helped me figure it out: Your state unemployment office should have sent you Form 1099-G by the end of January showing exactly how much you received in unemployment benefits. If you didn't get it or lost it, you can usually download it from your state's unemployment website. The key thing to remember is that unemployment benefits are treated as ordinary income, so they get added to your W2 wages and taxed at your regular tax rate. Since you made $29,800 from work plus $36,500 in unemployment, your total taxable income would be $66,300 (assuming you're filing single with standard deduction). I used the IRS withholding calculator on their website to get a rough estimate, but honestly ended up using TurboTax because it walked me through everything step by step. The good news is that if you owe more than $1,000, you can set up a payment plan with the IRS - they're actually pretty reasonable about it. One thing I wish I'd known earlier: you can request tax withholding from future unemployment benefits by filing Form W-4V with your state. Would have saved me this headache!