Just a heads up, the rules about EV tax credits changed again this year. Teslas assembled in North America might qualify for the $7,500 credit depending on battery component sourcing. The Model 3 RWD version I think is eligible for the full credit now because of the battery changes. But that's separate from your business deduction. If you're under 50% business use, you're stuck with just mileage deduction like others have said. One thing to consider is trying to legitimately increase your business use percentage. Could you consolidate personal errands to use another vehicle and use the Tesla primarily for business? The more you can document legitimate business use, the better your deduction.

Great question about the Tesla Model 3! Since you're tracking business miles and expecting under 50% business use, the standard mileage deduction is likely your best bet. For 2025, that's around 68.5 cents per business mile as Emma mentioned. One thing to keep in mind - even if you start with the standard mileage rate, you can potentially switch to actual expenses/depreciation in future years if your business use percentage increases. But you can't go the other way around. Also, don't forget to factor in the potential EV tax credit when calculating your overall tax benefits. The Model 3 eligibility has been changing based on battery sourcing requirements, so it's worth checking the current status when you're ready to purchase. For record keeping, I'd recommend using one of those mileage tracking apps like MileIQ or Everlance that others have mentioned. Having automated tracking makes it much easier to prove your business use percentage if the IRS ever questions it. The key is being consistent and having solid documentation from day one.

Has anyone had success deducting their health insurance premiums as a medical courier? I'm spending almost $900/month and I've heard conflicting advice about whether it's fully deductible or not.

As someone who's been doing courier work for a few years, I can't stress enough how important it is to keep meticulous records from day one. That 145K miles annually is going to be your biggest deduction - potentially worth over $99K at the current rate. A few additional tips that helped me: 1. Open a dedicated business checking account immediately. Keep ALL business expenses separate from personal. This makes bookkeeping so much easier and looks more professional if you ever get audited. 2. Consider getting a business credit card for gas and maintenance. Many offer cash back on gas purchases, plus it automatically separates your business expenses. 3. Don't forget about smaller deductions that add up: phone bill (business portion), GPS/navigation apps, work uniforms/safety gear, and even things like hand sanitizer or masks if required for medical deliveries. 4. With that income level, you'll definitely want to max out retirement contributions. A SEP-IRA lets you contribute up to 25% of your net self-employment income, which could significantly reduce your tax burden. 5. Keep receipts for EVERYTHING vehicle-related even if you use standard mileage. If your car gets totaled or needs major repairs, you might want to switch methods mid-year. The key is staying organized from the start. It's much harder to reconstruct records later, especially with the IRS scrutinizing high-mileage claims more closely these days.

Just a heads up, there's another angle to consider. If you claim Section 179 on a vehicle over 6,000 lbs GVWR (gross vehicle weight rating), you get more favorable tax treatment. Might be worth looking at trucks in that category. Also, don't forget about the possibility of bonus depreciation instead of Section 179. The rules and limitations are different, and in some cases it might be more advantageous depending on your overall tax situation.

One thing I haven't seen mentioned yet is the potential impact on your quarterly estimated tax payments. Since you're dealing with a significant tax hit from the rental property sale ($140k capital gains + $32k depreciation recapture), you'll likely need to make estimated payments to avoid underpayment penalties. If you're planning to buy the truck this year to take advantage of Section 179, make sure to factor that deduction into your estimated payment calculations. The IRS expects you to pay as you go, so if your withholding from your W2 job plus any estimated payments don't cover at least 90% of this year's tax liability (or 100% of last year's if your AGI was over $150k), you could face penalties even if you get a refund when you file. Also, since your side business income is subject to self-employment tax, the Section 179 deduction will save you not just on income tax but also on the 15.3% SE tax portion, which adds up to meaningful savings on a $30k+ deduction.

Just wanted to add - whatever you do, KEEP DETAILED RECORDS of every interaction. Note the date, time, who you spoke with, and what was said. This saved me when I had a similar issue. I ended up having to go through a formal appeal process for a state tax issue, and they tried claiming I never responded to their initial notice. I had documentation of three phone calls and two written responses that proved otherwise, and that's what ultimately got the penalties waived.

I went through something very similar a few months ago and it was absolutely nerve-wracking! Here's what I learned from my experience: First, definitely verify this is legitimate by calling the Department of Revenue using the number from their official website, not the letter. Once you confirm it's real, gather ALL your documentation - TurboTax confirmations, bank statements showing any tax payments, and screenshots of your filing status. The most important thing is to act quickly but don't panic-pay. I made the mistake of waiting too long thinking it would resolve itself, and the penalties kept growing. Call them ASAP and explain you believe there's been an error. Many states will put a temporary hold on penalties while investigating if you can show reasonable cause for disputing. In my case, it turned out TurboTax had a glitch where my state payment didn't process even though I got a confirmation. The state was very understanding once I provided my bank statements showing the payment attempt and TurboTax records. Also, send everything certified mail if you need to submit documents - that way you have proof they received it. Don't just rely on phone calls for important communications. You've got this! Most of these issues are processing errors that can be resolved with persistence and good documentation.

I was in a similar situation last year and completely panicked about the tax implications! After doing tons of research and even consulting with a tax professional, I can confirm what others have said - depositing your own cash into Cash App is absolutely NOT a taxable event. The $850 you've deposited is money you already had, so there's no new income being created. It's exactly like taking cash from your wallet and putting it in your bank account. The IRS doesn't care what format your existing money is in - physical cash, bank account, or digital wallet. Cash App will only send you a 1099-K if you RECEIVE payments from other people for goods or services over $600 in a year. Your own deposits don't count toward this threshold at all. So unless you're also selling things or providing services through the app, you shouldn't receive any tax forms from them. Keep records showing these were your own funds being deposited (maybe note the dates and amounts), but you definitely don't need to report these deposits as income on your tax return. You're overthinking this - you're totally fine!

I totally understand the anxiety around this! I had the exact same worry when I started using Cash App more frequently. The bottom line is that you're absolutely fine - depositing your own cash into Cash App is not taxable income, period. Think of it this way: if you took that same $850 and deposited it into a regular bank savings account, would you owe taxes on it? Of course not! Cash App is just another way to store your money digitally. The IRS only cares about NEW income you earn, not moving existing money between different accounts or formats. The confusion often comes from hearing about 1099-K forms, but those are only issued when you RECEIVE payments from other people for goods or services exceeding $600 per year. Your own deposits never count toward that threshold because you're not receiving money from anyone else - you're just converting your physical cash to digital form. You mentioned this is "pocket money" you already had, so there's definitely no tax liability here. Just keep doing what you're doing to help your family, and don't stress about the tax implications of these deposits!