As someone who's been tutoring for 5+ years now, here's some practical advice: keep EVERYTHING separate. Get a separate bank account, use a dedicated payment app account for business only, and track every single expense related to tutoring. For your situation specifically, you can absolutely deduct mileage (keep a detailed log), any materials you create for students, a portion of your internet/phone if used for tutoring, and any specific reference materials you buy to help with tutoring. But your general college tuition? No - that's considered personal education even if it makes you a better tutor.

Hey just a heads up - dont forget about the quarterly estimated tax payments if you're making decent money from tutoring! I got hit with a penalty my first year because nobody told me about this. If you expect to owe more than $1000 in taxes for the year, you're supposed to make quarterly payments.

Have u looked into carpooling options? There are apps like Waze Carpool where u might find ppl going to the same area. Might be way cheaper than uber/lyft every day!

Another thing to consider is whether any of your rideshare trips qualify as business travel. If you occasionally travel to client meetings, conferences, or temporary work locations that aren't your regular workplace, those trips could be deductible. Keep detailed records of the business purpose, date, and cost for any trips that might qualify. Also, if you're self-employed or have a side business, trips related to that work (like going to meet clients or pick up supplies) are generally deductible business expenses. Just make sure to keep good documentation and separate business from personal trips. The key is understanding the difference between regular commuting (home to primary workplace) which isn't deductible, versus business travel which can be.

I'm still a bit confused about loan interest deductions. For example, if I use part of this personal loan to make improvements to my home office (I'm self-employed), would that portion of the interest be deductible as a business expense?

Great thread with lots of helpful information! I just wanted to add one more perspective as someone who recently went through this exact situation with a personal loan. The key thing that helped me was keeping detailed records from day one. Even though personal loan proceeds aren't taxable income (as others have correctly explained), I created a simple spreadsheet tracking: - Original loan amount and date received - Monthly payment amounts and dates - How I used the funds (categories like debt consolidation, home repairs, etc.) This documentation became invaluable later when I needed to reference it for tax purposes, especially when some of the loan went toward my small business expenses. One thing I learned the hard way: if you think there's ANY chance you might use even a small portion of the loan for business or investment purposes, track those expenses separately from day one. It's much harder to reconstruct that information later when tax time comes around. Also, regarding the earlier discussion about IRS resources - IRS Publication 535 (Business Expenses) has a good section on borrowed funds used for business purposes if that applies to your situation.

Thanks everyone for all the detailed recommendations! This has been incredibly helpful. I'm leaning towards the Fujitsu fi-8170 based on Molly's recommendation - the ultrasonic double-feed detection sounds perfect for our client document issues, and 70 ppm would be a huge upgrade from our current ancient scanner. @Skylar @Kelsey - the taxr.ai discussion is fascinating. I had no idea AI document processing had gotten that good for tax forms. Definitely going to look into that as an add-on once we get the new scanner up and running. @Norah @Jessica - same with the Claimyr service. We probably spend 10+ hours per week on IRS hold during busy season, so anything that can free up that time would pay for itself quickly. One more question for the group: for those using network-enabled scanners, do you have any security concerns with scanning sensitive tax documents over your office network? Our clients trust us with some pretty confidential stuff and I want to make sure we're not creating any vulnerabilities.

Just wanted to chime in as someone who went through this exact scanner shopping process last year! We ended up with the Fujitsu fi-8170 that Molly recommended and it's been fantastic. The speed difference during tax season was night and day compared to our old scanner. One tip I wish someone had told me - make sure to factor in the cost of replacement parts when budgeting. The pick rollers and separation pads need replacing every 200K-400K pages depending on usage. For the Fujitsu, a full maintenance kit runs about $150-200, which isn't bad considering how much we use it. Also seconding the security concerns Omar raised. We set ours up to scan directly to encrypted folders on our server rather than using cloud storage, just to keep everything in-house. The IT setup was straightforward but definitely worth having a professional configure it properly the first time. Good luck with whatever you choose - any of the scanners mentioned here will be a huge upgrade from what you're currently dealing with!

Just wanted to add one more important point that I learned the hard way - make sure you have good records of your home improvements before you calculate your basis! I almost missed out on about $15,000 in basis adjustments because I didn't keep receipts from a kitchen renovation I did 4 years ago. For the $250k exclusion to work properly on Form 8949, you need to calculate your gain correctly first (sales price minus basis). Your basis includes your original purchase price PLUS qualified improvements like renovations, additions, new roofing, etc. The higher your basis, the lower your gain, and the more likely you'll stay under the $250k threshold. I had to dig through old credit card statements and contractor invoices to reconstruct my improvement costs. If you're in the same boat, don't forget about things like new HVAC systems, flooring, bathroom remodels, deck additions, and even some landscaping costs. These can add up to tens of thousands in additional basis. The IRS Publication 523 has a good list of what qualifies as improvements vs. repairs. Improvements add to your basis, but regular maintenance and repairs don't.

I went through this exact situation last year and want to emphasize how crucial it is to get this right! Emma, you're absolutely on the right track questioning whether that $187k should show up on line 13 of Schedule 1 - it definitely shouldn't if your entire gain qualifies for the exclusion. The key thing that tripped me up initially was thinking I could just ignore the 1099-S since my gain was under $250k. That's wrong! You must report it, but here's the correct process: 1. Complete Form 8949 showing your sale details 2. In column (g), enter code "H" 3. In column (h), enter your excluded amount (up to $250k for single filers) 4. This flows to Schedule D, which should show zero taxable gain 5. Nothing should appear on Schedule 1, line 13 if fully excluded I also learned that keeping detailed records of home improvements is absolutely critical for calculating your basis correctly. I found an additional $12,000 in improvements I had forgotten about, which reduced my gain even further. Don't skip reporting the sale just because it's excluded - the IRS expects to see this transaction on your return since you received a 1099-S. Getting this wrong could trigger an audit or notices down the road.