Regarding question #3 about capital gains - be careful here. Yes, you can still claim the primary residence exclusion when you sell ($250k/$500k), BUT any depreciation you've taken must be "recaptured" and taxed at 25% when you sell, regardless of the exclusion. This catches a lot of people by surprise! So if you've taken $20k in depreciation deductions over the years, you'll owe $5k (25% of $20k) when you sell, even if the sale would otherwise be fully excluded from capital gains tax.

One thing I'd add to all this great advice - make sure you're keeping really detailed records of everything! I learned this the hard way when I got audited on my room rental situation. Keep receipts for all your expenses (utilities, insurance, maintenance, etc.), track exactly how much rent you collect each month, and document the square footage or room allocation you're using for your deductions. I created a simple spreadsheet to track monthly rental income and expenses, and took photos of the rented rooms with measurements. Also, consider opening a separate bank account for your rental income and expenses - it makes everything much cleaner come tax time. The IRS loves good documentation, and if you ever get questioned about your deductions, having everything organized will save you a lot of headaches. The depreciation recapture issue that @b7a3f4da667a mentioned is real, but don't let it scare you away from taking the deduction. The tax savings now usually outweigh the recapture cost later, especially with inflation. Just factor it into your long-term planning!

Don't forget to keep copies of EVERYTHING and proof of mailing! I made the mistake of not keeping good records when I mailed multiple returns last year. The IRS lost one of my returns, and I had to resend it. Now I scan all returns before mailing and get a certificate of mailing from the post office for each envelope (cheaper than certified mail but still gives you proof).

Adding to what everyone else has said about mailing separately - I work as a tax preparer and can confirm that separate envelopes is definitely the way to go. The IRS processing centers have different workflows for different tax years, and mixing them up can cause delays. One thing I haven't seen mentioned yet is to make sure you're using the correct mailing address for each tax year. The IRS sometimes changes processing center addresses between years, so double-check the instructions for 2022 vs 2023 returns. Also, if you owe money on both years, consider which one to prioritize if you can't pay both at once - generally you want to pay the older year first since penalties and interest accumulate longer on those. Good luck getting caught up! Don't stress too much - the IRS deals with late returns all the time.

Ive been dashing for 3 years now alongside my office job. Keep EVERY receipt - gas, phone chargers, hot bags, etc. The tax write offs make a HUGE difference. Also dont forget about the quarterly payments! I put reminders in my calander cause I forgot the first year and got hit with penalties.

Great question! I started doing Doordash last year while working my regular job and learned a lot through trial and error. Here's what I wish I knew from the start: You'll definitely want to track your mileage religiously - it's usually your biggest deduction. I use a simple notebook in my car and jot down my starting/ending odometer readings for each dash session. The standard mileage rate for 2024 is 67 cents per mile, which adds up fast! For the quarterly payments, you can also ask your regular employer to withhold extra taxes from your paycheck instead of making separate estimated payments. I had my HR department take an extra $150 per month from my regular job to cover the Doordash taxes - much easier than remembering quarterly deadlines. One tip: keep a separate envelope or folder for ALL your Doordash-related receipts. Car maintenance, phone accessories, insulated bags, even hand sanitizer you buy for deliveries. These small expenses add up and reduce your taxable income. And definitely set aside that 25-30% of earnings right away. I learned the hard way that it's much easier to save as you go than scramble to pay a big tax bill in April!

Has your friend checked if there are any specific provisions for the Robinson Huron Treaty in the US-Canada tax treaty? Some indigenous rights agreements have special handling. Also, remember that state taxation is a whole separate issue from federal. Some states are more aggressive about taxing foreign income than others. Which state does your friend live in? That could make a big difference in the overall tax burden.

This is definitely a complex situation that requires careful documentation. One thing I'd add to the excellent advice already given is that your friend should request detailed documentation from the Robinson Huron Treaty settlement administrators about the specific nature and classification of the payment. The IRS will want to see clear documentation showing whether this is compensation for historical land claims, income replacement, or another type of settlement. Having this upfront documentation could save your friend from potential audit issues down the line. Also, given that he's a Canadian citizen residing in the US, he may need to consider his filing obligations in both countries. Canada might still have tax implications even if there are indigenous exemptions, and the US will definitely want their share as he's a US tax resident. I'd strongly recommend setting aside at least 25-30% of the settlement amount for taxes until he gets professional guidance. Better to be over-prepared than caught short when tax time comes around.

Quick question - has anyone used TurboTax to file with an EIDL grant? Is there a specific place where you enter this or do you just not include it as income? Don't want to mess this up!

Great question! As others have mentioned, the EIDL grant portion is generally not taxable at the federal level under Section 139 of the Internal Revenue Code. However, I want to emphasize something that's been touched on but is really important - make sure you keep detailed records of exactly how you used those grant funds. Even though the grant isn't taxable income, the IRS still wants to see proper documentation if you're ever audited. I'd recommend creating a simple spreadsheet showing the grant amount, the date received, and specifically what business expenses you paid with those funds (rent, utilities, payroll, etc.). Also, since you mentioned you're between accountants, when you do find a new one, make sure they're familiar with EIDL grant treatment. Some preparers who don't deal with small business clients regularly might not be up to speed on the current rules. Good luck with your filing!