One additional consideration that hasn't been mentioned - if you're planning to move closer to your new job, make sure you understand the timing requirements for the Section 121 exclusion. You need to have used the home as your primary residence for at least 2 of the 5 years before the sale. Since you've lived there for 5 years already, you have some flexibility. But if you rent it out for 2 years and then sell, you'll be right at that 5-year lookback period. If for any reason the sale gets delayed (market conditions, finding buyers, etc.), you could potentially lose eligibility for the exclusion. Also, consider whether renting it out for just 2 years makes financial sense after factoring in landlord responsibilities, potential vacancy periods, property management costs, and the tax complexity it creates. Sometimes the headache isn't worth the extra income, especially if you're not planning to be a long-term landlord. You might want to run the numbers on selling now versus the rental income minus all associated costs and taxes.

Great discussion everyone! I'm actually a tax professional and wanted to add a few clarifications to help @Melina Haruko and others in similar situations. First, the Section 121 exclusion is indeed available as long as you meet the 2-out-of-5-year test, but there's an important nuance: if you claim depreciation during the rental period (which you're required to do), that portion of the gain will be subject to depreciation recapture at 25%, even if you qualify for the exclusion on the remaining gain. Second, regarding the tools and services mentioned - while they can be helpful, I'd strongly recommend consulting with a tax professional for your specific situation, especially given the complexity of partial-use properties. The IRS rules around this are quite detailed and small mistakes can be costly. Finally, @Zara Rashid made an excellent point about timing. Consider not just the tax implications, but also the practical aspects: property management from a distance, market timing risks, and whether the net rental income (after all expenses and taxes) justifies the complexity. Sometimes the cleanest financial move is to sell before converting to rental property. Feel free to ask if you have specific questions about the tax calculations!

Carmen, you're definitely not alone in feeling overwhelmed by delivery driver taxes! I just went through this same learning curve last year. One thing I'd add to all the great advice here is to start tracking your income and expenses RIGHT NOW, even if tax season feels far away. I made the mistake of trying to reconstruct everything from memory and bank statements later - it was a nightmare. Create a simple spreadsheet or use an app to log your daily earnings and any business expenses as they happen. Also, since you mentioned you're doing this mostly on weekends, make sure to track those miles even if it feels like "just" weekend work. Weekend driving often means longer distances to busier areas, so those miles really add up! And don't stress too much about getting everything perfect your first year. The IRS understands that gig work is new for a lot of people. Just keep good records and be honest about your income and legitimate business expenses. You've got this!

Carmen, I totally feel your stress about this! I was in the exact same boat when I started doing delivery work. Here's my simplified breakdown for getting started: **Immediate action items:** 1. Download a mileage tracking app TODAY (Stride, MileIQ, or even Google Maps timeline) 2. Start a simple expense log - even just notes in your phone 3. Open a separate savings account and put 25-30% of each week's earnings in there **What you CAN deduct:** - All business miles (including driving to hotspots, between deliveries, etc.) - Hot bags, phone mount, car charger - Portion of phone bill (maybe 20-30% if used primarily for work) - Car washes if done specifically for delivery work - Hand sanitizer, tissues, other supplies **Forms you'll need:** - 1099-NEC from Uber (if you make over $600 total) - Schedule C for your tax return - Form SE for self-employment tax The biggest mistake I made my first year was not tracking miles from day one. Don't be like me! Even if you only work weekends, those miles to busy areas really add up. And remember - you're learning, and that's okay. The IRS isn't trying to trick you, they just want accurate reporting. You've got this! The fact that you're asking these questions now shows you're already ahead of where I was. 🙂

Regarding the IRS Free Fillable Forms option - this is essentially the electronic equivalent of filling out paper forms manually. There's minimal guidance, no calculational assistance between forms, and no error-checking beyond basic math. I would not recommend this approach unless you have a good understanding of which tax forms you need and how they interrelate. For cryptocurrency transactions, FreeTaxUSA does support reporting these, though you'll need to manually enter the information rather than having it automatically imported. If you have a significant number of transactions, this could be time-consuming but would still likely save you money over TurboTax's premium pricing.

I've been using FreeTaxUSA for the past two years after making a similar switch from TurboTax, and I can confirm your experience is spot on. The math is identical because they're all following the same tax code - you're basically paying TurboTax's premium for brand recognition and a slightly more polished interface. One tip for anyone considering the switch: if you have multiple investment accounts or a lot of transactions, take note of how much time the manual entry adds. For me, it's maybe an extra 30-45 minutes total, which is absolutely worth it for the $150+ savings. Also worth mentioning that FreeTaxUSA's customer support has been surprisingly good the few times I've needed it. Not that I needed much hand-holding, but they were responsive and knowledgeable when I had a question about a specific deduction. The biggest adjustment was just getting used to a slightly different interface flow, but honestly after the first year it felt completely natural.

Quick question - does a legal separation need to be finalized before tax time to affect your filing status? My wife moved out in December and we're getting separation paperwork started but it won't be done before April.

I went through something very similar last year when my husband and I separated but hadn't finalized our divorce yet. Since you're still legally married as of December 31st, you can only file as married filing jointly or married filing separately - not single or head of household. Given that your finances are completely separate now and you're concerned she might file jointly without telling you, I'd strongly recommend married filing separately. This protects you from being liable for any tax issues on her side, and since you mentioned you're not communicating much, it eliminates the need to coordinate your filing. The downside is you'll likely pay more in taxes than if you filed jointly, but the peace of mind is usually worth it during separation. Since you're paying the mortgage alone even though her name is still on the house, make sure you can still claim the mortgage interest deduction - you should be able to since you're the one actually making the payments. You might want to consult with a tax professional who can run the numbers for both scenarios and show you exactly what the difference would be in your specific situation.

One thing nobody's mentioned - make sure you have SOLID documentation for those expenses if they were from 2023 but you're claiming them in 2024. The IRS tends to flag mismatched years, especially with new businesses. Keep receipts, bank statements, credit card statements, and maybe even take photos of the equipment showing you still own and use it. Better safe than sorry!

Great question! I went through something similar with my photography business. The key thing to understand is that the IRS distinguishes between when you incur expenses and when your business actually begins operations. Since you didn't start generating income until 2024, that's when your business truly "began" for tax purposes. You can definitely claim those 2023 expenses on your 2024 return. For the equipment (mowers, trimmers, etc.), you'll likely want to look into Section 179 deduction which allows you to deduct the full cost of qualifying equipment in the year you place it in service for your business - which would be 2024 in your case. The utility trailer might be handled differently depending on its weight and use, but don't worry about losing those deductions. Just make sure you keep all your 2023 receipts and any documentation showing when you actually started operating the business in 2024. The IRS is pretty reasonable about startup situations like this as long as you have good records.