I work at a volunteer tax prep site, and we've dealt with this issue a lot. The solution depends on which stimulus payment we're talking about: 1st & 2nd payments (2020): You'd need to amend your 2020 return if you haven't already claimed them 3rd payment (2021): You'd need to amend your 2021 return The easiest approach now would be to file the amended returns using Form 1040-X and claim the Recovery Rebate Credit for the payments you never cashed. Keep those expired checks though! The IRS might request documentation later. Also, there's a time limit to claim these credits - generally 3 years from the original filing deadline. So for 2020 returns (1st & 2nd stimulus), you have until April 15, 2024. For 2021 returns (3rd stimulus), you have until April 15, 2025.

I went through this exact situation last year! I had two expired stimulus checks from when I was deployed overseas. Here's what worked for me: First, try calling the IRS at 800-919-9835 and ask specifically for the "Economic Impact Payment" department. When you get through (which can take forever), tell them you have expired stimulus checks and need to request a payment trace. They'll ask for the check numbers, amounts, and issue dates if you have them. The agent will initiate a trace to confirm the checks were never cashed, then they can reissue new payments. This took about 8-10 weeks for me, but I did get replacement checks for the full amounts. One tip: if you decide to go the amended return route instead, make sure you're claiming the right tax year for each payment. The first two stimulus payments go on your 2020 return, and the third one goes on your 2021 return. You can't mix them up or it'll delay processing. Either way, definitely keep those expired checks as proof - the IRS may ask for copies during their review process. Good luck getting your money back!

One thing to consider that hasn't been fully addressed is the cash flow impact of your decision. With Section 179 deduction on a purchased van, you get a huge tax benefit upfront but you're also tying up a lot of capital (or taking on debt payments). As a fellow event photographer, I know how unpredictable our income can be - some months are feast, others are famine. Leasing gives you more predictable monthly expenses and preserves your cash flow for other business investments like new equipment or marketing. That said, if you're confident in your revenue growth (35% is impressive!) and have good cash reserves, buying with Section 179 could save you thousands in taxes. Just make sure you can handle the financial commitment without putting your business at risk during slower periods. Also, don't forget to factor in maintenance costs - with a lease, major repairs are usually covered, but with ownership, that's all on you. Cargo vans are generally reliable, but when you're loading/unloading heavy equipment daily, things can wear out faster than expected.

One important consideration that hasn't been mentioned is the Section 199A deduction (Qualified Business Income deduction). If you're eligible for this 20% deduction as a sole proprietor, the timing of your vehicle deduction can impact your QBI calculation. If you take the full Section 179 deduction in year one when purchasing, it reduces your taxable business income, which could potentially reduce your Section 199A deduction benefit. With leasing, the deductions are spread out over time, which might allow you to better optimize both deductions across multiple years. This is especially relevant given your 35% revenue growth - you might want to model out a few scenarios to see how the vehicle deduction timing affects your overall tax situation. The interaction between these deductions can be complex, and what looks best on paper for vehicle expenses alone might not be optimal when you consider your full tax picture. Also worth noting - if you do buy and take Section 179, make sure you understand the recapture rules if you ever sell the van or change its business use percentage. The IRS can require you to "pay back" some of those deductions if circumstances change.

4 I had a similar sales business with big contractor expenses and ended up getting audited because of this exact issue. Make sure you also have business justification for each contractor - showing WHY you needed their services and how they related to your revenue generation. That was the first thing the IRS asked me about, even before wanting to see proof of payments or 1099s. For what it's worth, the auditor told me that while missing 1099s might trigger a review, what they're really looking for is whether the expenses are legitimate and reasonable for your business type and size. In my case, having detailed contracts with clear work deliverables was what ultimately saved me. For your S-Corp transition, this is even more important because the IRS scrutinizes S-Corps more closely for both unreasonable compensation issues and expense substantiation.

This is a really common issue for small businesses, and I appreciate everyone sharing their experiences here. One thing I'd add that hasn't been mentioned yet is the importance of backup withholding requirements. When contractors refuse to provide W-9s, you're technically supposed to withhold 24% of their payments for backup withholding and send that to the IRS. Most small business owners don't know this rule, and since you've already paid them in full, you can't go back and collect it now. However, documenting that you requested the W-9s multiple times (and their refusal) is crucial. The IRS understands that you can't force someone to provide their tax information, but they expect you to make reasonable efforts. For your S-Corp transition, definitely get a solid contract template that requires W-9 completion before any payments are made. I learned this lesson the hard way after dealing with similar contractor issues. Also, consider requiring new contractors to complete their tax forms as part of your onboarding process rather than waiting until tax season. Your 75% deduction rate will definitely get attention if you're audited, but if you have legitimate business expenses with proper documentation showing the work was actually performed and necessary for revenue generation, you should be fine. Just make sure every expense has a clear business purpose that you can articulate.

One thing to consider - if your employer offers any kind of tuition reimbursement program, that might be a better route than trying to deduct it yourself. My company reimburses CDL training costs if you stay with them for at least a year. Worth asking your HR department if they have something similar before going through the tax deduction headache!

Hey Ashley! I'm in a similar boat - got my CDL about 6 months ago and paid for the training myself. After reading through all these responses, I'd definitely recommend looking into the Lifetime Learning Credit that Oliver mentioned. I initially overlooked it because I thought it only applied to traditional college courses, but it turns out vocational training like CDL school can qualify too. The key thing I learned is that even though we can't deduct the training costs directly as W-2 employees (thanks to the 2018 tax law changes), the credit can still save you real money - up to 20% of qualified expenses. Since your training was $8,100, you could potentially get back up to $1,620 if you qualify income-wise. I'd suggest gathering all your CDL school documentation - receipts, loan statements, curriculum info - and either use one of those analysis tools people mentioned or talk to a tax professional who knows transportation industry stuff. Don't give up on getting some tax benefit from this investment!

Warning from personal experience: be super careful about mixing personal and business use with that Tesla rental! I did something similar last year and got audited because I couldn't properly document my business percentage. Make sure you're taking photos of your odometer at the beginning and end of EVERY shift, and maybe even use a backup tracking app too. The IRS is really cracking down on gig workers claiming 100% business use when they're actually using vehicles for personal stuff too. My tax bill ended up being crazy high because they disallowed a bunch of my deductions. Don't make the same mistake!

Great question about the Tesla rental deduction! I've been doing rideshare taxes for several years and can confirm that you're on the right track. When you rent a vehicle specifically for business use, you can indeed deduct the rental costs as a business expense rather than using the standard mileage rate. For your situation with switching mid-year, you'll need to keep separate records for each period: - Personal vehicle period: Use standard mileage deduction based on business miles driven - Rental period: Deduct actual rental costs (business percentage only) A few important tips from my experience: 1. Keep detailed records of when you switch vehicles - exact dates matter 2. Track your business vs personal usage percentage for the rental meticulously 3. Save all rental agreements and payment receipts 4. Consider using a mileage tracking app to document business use The fact that it's an official Uber partner rental program actually helps support the legitimacy of the business expense. Just make sure you're honest about the business percentage - the IRS can cross-reference your claimed usage with your actual trip data from Uber if they audit you. Good luck with the Tesla rental! Many drivers find the electric vehicle savings make it quite profitable once you factor in the tax benefits.