I'm confused about something related to this... if I have both W-2 income from my main job AND 1099 income from side gigs, do I combine them or file separately? My 1099 is only like $900 but my W-2 job pays over $45k.

Just to add one more important point that might help you feel less overwhelmed - even though you need to file, the good news is that with only $1,924 in DoorDash income, your actual tax burden will likely be pretty small after deductions. Don't forget you can deduct business expenses like: - Mileage (probably your biggest deduction - 67¢ per business mile for 2024) - Phone bill percentage (if you use it for deliveries) - Insulated delivery bags - Car phone mounts or other equipment - Even parking fees or tolls during deliveries Many gig workers find that after legitimate business deductions, their net profit drops significantly, which reduces both their income tax and self-employment tax. The self-employment tax on your net earnings will be around 15.3%, but you also get to deduct half of that self-employment tax when calculating your income tax. Since this is your first time with 1099 income, consider using tax software that handles Schedule C and Schedule SE, or consult with a tax professional to make sure you're claiming all eligible deductions.

But wait - doesn't the FAA require flight logs anyway? Couldn't you just use those same logs to mark which flights were business vs personal? Seems like aircraft would actually be easier to track than cars since there's already mandatory record keeping.

Your friend is definitely confused about the GSA vs IRS distinction. As a tax professional, I see this mistake frequently with pilots and boat owners who think there are standard mileage rates for all vehicles. The $1.74/mile GSA rate is specifically for federal employees using personal aircraft on official government business - it's a reimbursement rate, not a tax deduction. The IRS Publication 463 is crystal clear that standard mileage rates only apply to "automobiles, vans, pickups, and panel trucks." For his Cessna, he needs to track actual expenses (fuel, oil, annual inspections, insurance, hangar rent, depreciation) and multiply by his business use percentage. The good news is this often results in larger deductions than any hypothetical standard rate would provide, especially when you factor in depreciation on the aircraft value. Tell your friend to keep detailed logs of business flights with dates, destinations, business purpose, and passengers. The IRS loves documentation when it comes to aircraft deductions since they're frequently audited.

Has anyone used a 1031 exchange to defer taxes when selling land after a fire? I'm wondering if that's possible in this kind of situation.

One important thing to consider is the timing of when you convert the property from personal use to investment property. Since you've held the vacant land for several years after the fire and now live elsewhere, the IRS may view this as investment property rather than personal property. This distinction matters because it affects both your depreciation options (you can't depreciate land, but the holding period and intent matter for capital gains treatment) and potentially your ability to use installment sale reporting if you're considering seller financing. Also, make sure to gather all your documentation now - original purchase documents, insurance settlement papers, property tax assessments from before the fire, and any records showing when you established your new primary residence. The IRS likes to see a clear paper trail for these types of transactions, especially when there's been a casualty loss involved. If you're looking at a significant capital gain, you might also want to consider timing the sale strategically - perhaps in a year when you have other capital losses to offset, or if you expect to be in a lower tax bracket.

When I moved to the US from Canada I was so confused by the tax year thing! In my home country we have a totally different system. One question though - what tax year do you use for reporting investments that you've held for multiple years? Is it the year you sell the investment?

This is such a common confusion! I went through the exact same thing when I first started working. Here's what helped me understand it: Think of the tax year like a school year - it's a complete 12-month period that gets "graded" (filed) after it's over. So your 2024 tax year (Jan 1 - Dec 31, 2024) gets filed during the 2025 filing season (Jan - April 2025). For your March 2024 job situation, that income definitely goes on your 2024 tax return that you'll file in early 2025. Your employer should send you a W-2 by January 31, 2025 showing all the income and taxes withheld from that job. The key thing that clicked for me: we always file taxes for a COMPLETED year, never for the year we're currently living in. That's why when you file in April 2025, you're not including any 2025 income - that year isn't complete yet! And yes, the system is unnecessarily complicated. Most other countries make it much simpler, but we're stuck with this backwards-looking annual system.

Does anyone know if this is different for LLC vs sole proprietor? I have a single-member LLC but file Schedule C.

This is such a common confusion point for self-employed folks! I went through the exact same thing when I started my consulting business. The key is proper documentation - make sure your invoices clearly separate the reimbursed expenses from your service fees. I use a simple format like "Service Fee: $X, Travel Reimbursement: $Y" on each invoice. This makes it crystal clear to both you and the IRS that these are genuine reimbursements, not additional income. One tip that helped me: I keep a separate spreadsheet tracking each reimbursed expense with the corresponding receipt and invoice number. Makes tax time so much easier and gives you bulletproof documentation if questions ever come up. TurboTax handles this pretty well if you enter everything in the right categories - just make sure you're consistent about how you classify things. The peace of mind of doing it right from the start is definitely worth the extra bookkeeping effort!