I do bookkeeping for several digital nomads in similar situations. One thing nobody mentioned yet - if you form an S-Corp for your 1099 work and become an employee of your own corporation, you can potentially have your corporation reimburse you for travel under an "accountable plan" which could be more advantageous than taking Schedule C deductions. Might be worth looking into depending on your 1099 income level.

The S-Corp discussion is interesting, but there's another angle worth considering for your rental property income. If you're traveling to different locations and occasionally visiting your rental property for legitimate business purposes (inspections, meeting with contractors, handling tenant issues), you might be able to deduct those specific travel costs against your rental income even if the primary trip purpose was for your remote work. The key is documentation - keep records of any rental-related activities during your travels. Even a brief property inspection or meeting with a local property manager could make that portion of your travel deductible. Just make sure to allocate expenses properly between personal, 1099 business, and rental business purposes. Also, consider the home office deduction implications more carefully. If you're claiming a home office for your 1099 work, you'll need to reduce that deduction for the time you're away working from temporary locations. The math can get complex, but sometimes the temporary workspace deductions while traveling can actually exceed what you'd lose from the reduced home office deduction, especially if you're working from expensive locations.

I work at a bank and see this confusion ALL THE TIME. Here's the simple version: one-time payments between family members are almost never taxable to the recipient. The $10,000 reporting threshold some people mention is for CASH transactions and bank reporting requirements, not for taxation purposes, and it doesn't apply to Venmo anyway. The $600 reporting threshold is for BUSINESS transactions on payment apps. From what you described, your $2000 is clearly a personal payment and not something you'd need to report as income. Just make sure your cousin doesn't label it as "car repair services" or something business-sounding in the description.

Great question! Based on what you've described, you shouldn't have to worry about taxes on this $2000 payment. Since this is a one-time payment from your cousin for helping with his truck repair, it would likely be classified as either a gift or personal reimbursement rather than taxable income. The IRS distinguishes between casual help among family members and running an actual business - you're clearly in the former category. The key factors working in your favor are: it's a family member, it's a one-time occurrence, you're not in the business of car repair, and it's essentially compensation for your time and parts you purchased. Even though $2000 is a substantial amount, the nature of the payment matters more than the dollar amount for tax purposes. Just make sure your cousin sends it as a personal payment (friends/family option) rather than marking it as goods and services. Keep a simple record of what the payment was for in case you ever need to explain it later, but this definitely doesn't sound like something you'd need to report as income on your tax return.

Great question about vehicle deductions! I've been through a similar analysis for my own business. A few additional considerations that might help: 1. **Timing matters for S-corp elections** - Since your LLC is taxed as an S-corp, make sure your vehicle purchase timing aligns with your tax year planning. If you're trying to drop tax brackets, consider whether spreading the deduction over multiple years via depreciation might actually be more beneficial than trying to maximize first-year deductions. 2. **Documentation is critical** - Whatever route you choose (standard mileage vs. actual expenses), start tracking business use immediately and contemporaneously. The IRS is particularly strict about vehicle deductions, and you'll need detailed mileage logs showing business purpose, destinations, and dates. 3. **Consider lease vs. buy** - Given your expanding family situation, a lease might offer more flexibility. Lease payments are generally easier to deduct (just the business use percentage), and you won't face recapture issues if your business use changes when your wife starts using it full-time. 4. **State tax implications** - Don't forget to check how your state handles vehicle deductions, especially with the S-corp structure. Some states have different rules that could affect your overall tax strategy. The Honda Odyssey is a great family vehicle, but as others noted, the luxury auto limits will significantly impact your deduction strategy. You might want to run the numbers on both the depreciation method and standard mileage rate to see which works better for your specific situation.

One thing to keep in mind with the S-corp structure is the additional compliance burden if the company owns the vehicle. You'll need to maintain detailed records not just for the IRS, but also to properly handle the personal use reporting on your W-2. I'd actually recommend considering a different approach: have the S-corp establish an accountable reimbursement plan and keep the vehicle in your personal name. This way you can use either the standard mileage rate or actual expense method, get reimbursed by the company for business miles, and avoid the fringe benefit complications entirely. With 15,000 annual business miles, you're looking at roughly $10,000+ in annual reimbursements (at current rates), which is deductible to the S-corp and not taxable income to you. Plus, if your usage changes when your wife takes over, there's no recapture or complicated asset transfers to deal with. The key is setting up the accountable plan properly with adequate substantiation requirements. Your CPA can help draft the plan documents to ensure compliance.

I'm actually dealing with this exact situation right now! I've been booth renting at a grooming salon for about 8 months and went through the same worry spiral when someone told me it might be "illegal." After doing tons of research and even consulting with a small business attorney, I can confirm that what you're describing is totally legitimate. The key thing that helped me feel confident was understanding that the IRS isn't trying to shut down legitimate independent businesses - they're going after situations where employers are dodging payroll taxes by incorrectly labeling employees as contractors. Your setup sounds identical to mine: I have my own clients who call me directly, I set my own hours and prices, handle my own payments through Square, carry my own liability insurance, and file as self-employed. The salon owner and I have a simple month-to-month rental agreement for the table space, and that's it. One thing that really put my mind at ease was learning that this business model has been around for decades in our industry. Most of the groomers I know started out this way before eventually opening their own shops. If it were actually illegal, the IRS would have shut it down long ago! The people commenting on that ad probably don't understand the difference between legitimate booth rental and employee misclassification. Don't let the noise discourage you - you're running your business the right way.

I've been booth renting as a dog groomer for over 3 years now and can definitely confirm this is a completely legal and common arrangement! The confusion usually comes from people not understanding the difference between legitimate independent contractor relationships and employee misclassification. What you're describing sounds exactly like how proper booth rental should work. The fact that you have your own clients, set your own prices, handle your own payments, and maintain complete control over your business operations clearly establishes you as an independent contractor, not an employee. The owner being a groomer herself actually doesn't matter at all legally - plenty of salon owners work alongside their renters. She's essentially wearing two hats: business owner/landlord and fellow service provider. One tip that's helped me: I keep really clear documentation of the independent nature of my business. Things like my business license, separate liability insurance policy, my own business cards, and records showing I handle all my own client communications and payments. During a routine audit last year, the IRS reviewer said these types of records make it immediately obvious that we're running separate businesses. Don't let the negative comments discourage you or your salon owner. This business model has been successfully used in our industry for decades. The people posting those comments likely don't understand the nuances of legitimate booth rental vs. employee misclassification.

Sophia, this is such an inspiring discussion to read! Your thoughtful approach and genuine desire to help people really comes through. As someone who's worked in financial services, I can tell you that having that combination of technical knowledge (bookkeeping degree, math skills) and personal understanding (doing family taxes, immigrant background) is incredibly valuable. One thing that struck me is how this thread has showcased the evolution of the tax industry - from traditional preparation to AI-assisted tools like taxr.ai for accuracy, to services like Claimyr for IRS communication efficiency. As a newcomer, you're actually entering at a great time when technology can amplify your skills rather than replace them. I love the suggestions about the VITA program for hands-on training and potentially specializing in immigrant communities. That specialization could really set you apart, especially if you can combine it with modern efficiency tools. The seasonal nature that others mentioned is definitely something to plan for, but it sounds like you're approaching this thoughtfully rather than jumping in blindly. Your bookkeeping background will definitely help with the business side - understanding cash flow patterns, organizing client data, and maintaining professional standards. Best of luck with whatever you decide! This community seems to have given you some excellent guidance to help make an informed choice.

Reading through this entire thread has been absolutely fascinating! As someone who's been considering various side hustles, I'm impressed by how thorough and supportive this community is. @Sophia Rodriguez - your journey from considering tax preparation to having a clear roadmap is really inspiring. The combination of your bookkeeping background, family tax experience, and genuine desire to help people (especially immigrant families) seems like such a strong foundation. What strikes me most about this discussion is how it's evolved from basic viability questions to covering everything from certification paths (VITA program, EA certification) to modern technology tools (taxr.ai for accuracy, Claimyr for IRS efficiency) to specialization strategies. It really shows how much the tax preparation field has to offer for someone willing to approach it professionally. The seasonal nature and intensity seem manageable as a side hustle, especially with the potential for year-round client relationships through tax planning services. And the emphasis on proper insurance, business setup, and starting with supervised experience through VITA shows there's a clear path to do this right. This thread is a perfect example of how valuable community knowledge-sharing can be. Thanks to everyone who contributed their experiences and expertise!