This is definitely a legitimate arrangement when structured properly! Your situation actually looks really solid from a compliance perspective - having an established LLC with 3 years of operating history and multiple clients is exactly what the IRS likes to see. The key factors working in your favor are that video production is completely separate from project coordination work, you have genuine independent contractor credentials through your existing business, and you're charging market rates that reflect the specialized nature of the services. A couple of practical suggestions: **Review your employment agreement first** - Look for any clauses about outside business activities or IP ownership that might require disclosure or create conflicts. **Document the separation clearly** - Create a detailed scope of work showing exactly what your LLC provides versus your employee duties. This becomes your roadmap for maintaining proper boundaries. **Maintain business formalities** - Use your LLC's business email, accounting system, and equipment for all contractor work. Keep a simple log distinguishing when you're working in each capacity. **Keep diversified clients** - Continue serving your other clients so your employer doesn't become your dominant revenue source. The pricing difference you mentioned actually helps establish legitimacy - it shows this is professional contractor work, not disguised employee compensation. No special IRS forms needed for pre-approval, just proper documentation and clear separation between roles. This sounds like a great opportunity for both you and your employer!

Your situation sounds very promising from a legal standpoint! The fact that you have an established LLC with 3 years of operating history and existing clients is a huge advantage. This demonstrates to the IRS that you're running a legitimate business, not just trying to reclassify employee work to avoid taxes. The key is maintaining clear separation between your two roles. Since video production and project coordination are completely different skill sets, you're in good shape for meeting the IRS's "substantially different work" requirement. Here are the essential steps I'd recommend: **Document everything properly** - Create a formal contract between your LLC and the company that clearly outlines video production services. Keep this completely separate from your employment agreement. **Maintain business independence** - Use your LLC's business email, invoicing system, and equipment for all contractor work. Consider working different hours when possible to show behavioral independence. **Price appropriately** - Your LLC charging more than your employee rate actually works in your favor, as it demonstrates legitimate market-rate professional services. **Keep other clients** - Continue serving your existing clients so your employer doesn't become your sole revenue source. No special IRS pre-approval is needed, but having proper documentation will protect you if questions arise. The arrangement you're describing is quite common and works well when structured correctly. Good luck with your proposal!

As someone who recently went through a similar farm inheritance situation, I'd strongly recommend getting a qualified agricultural tax professional involved sooner rather than later. Farm inheritance taxation has so many specialized rules and exceptions that general tax preparers often miss important opportunities or make costly mistakes. One thing I learned the hard way is that the timing of cattle sales after inheritance can impact your tax liability. If you sell immediately after the date of death, you'll likely have minimal taxable gain due to the stepped-up basis. But if you hold the cattle and continue feeding them for months before selling, any weight gain or market appreciation becomes taxable income. Also, don't forget to consider the estate's tax year. If your grandmother passed away in 2024, the estate might need to file its own tax return (Form 1041) for any income earned between the date of death and final distribution to heirs. The cattle sales might need to be reported on the estate return rather than individual returns, depending on who technically owns them during the sale period. Keep detailed records of everything - feed costs, veterinary bills, sale prices, dates, and any expenses related to maintaining or selling the cattle after inheritance. These details will be crucial for properly calculating any taxable gain and taking advantage of all available deductions.

Just went through this exact situation with my family's dairy farm inheritance last year. One crucial detail that hasn't been mentioned yet - if your grandmother was claiming depreciation on any farm buildings, equipment, or breeding livestock over the years, there could be depreciation recapture taxes when those assets are eventually sold, even with the stepped-up basis. The stepped-up basis applies to the fair market value, but any depreciation previously claimed by your grandmother may need to be "recaptured" as ordinary income rather than capital gains. This especially applies to things like tractors, barns, milking equipment, etc. if they get sold as part of settling the estate. For the cattle specifically, if they were breeding stock that your grandmother held for more than 24 months, they might qualify for capital gains treatment rather than ordinary income, which could save you significantly on taxes. But if they were raised for sale (rather than breeding), different rules apply. I'd recommend gathering all of your grandmother's tax returns from the past few years, especially the Schedule F forms, before meeting with a tax professional. They'll need to see what depreciation was claimed and what accounting method was used to properly advise you on the cattle sale tax implications.

Don't overlook the potential mileage deduction! For 2023 its 65.5 cents per mile for business travel in your truck. If your driving a lot for these contracts that really adds up. Just make sure you keep a detailed mileage log (i use the stride app). You can either do actual expenses or the standard mileage rate but not both.

Just to add another perspective - I went through this exact same decision last year when I started my handyman business. I ended up going with a single-member LLC for the liability protection, especially since I'm working with power tools and heavy equipment on client properties. The peace of mind is worth the small additional paperwork. One thing I wish I'd known earlier: if you're buying that pickup truck, look into whether you qualify for the full Section 179 deduction (up to $1.16 million for 2023) vs. regular depreciation. For vehicles over 6,000 lbs GVWR used primarily for business, you might be able to deduct the full purchase price in the first year instead of depreciating it over time. This could be huge for your tax situation, especially if you're expecting a loss this year anyway. Also, keep every single receipt and document everything. The IRS gets picky about vehicle and equipment deductions, so having bulletproof records is essential.

I wanted to add something that hasn't been mentioned yet - look into whether your state offers any caregiver tax credits or deductions. Many states have started recognizing the financial burden on families providing full-time care for disabled adult children. Also, since you left your job to become a full-time caregiver, you might qualify for the Premium Tax Credit if you're getting health insurance through the marketplace. The loss of employer-sponsored coverage due to caregiving responsibilities could make you eligible for advance premium tax credits, which could significantly reduce your monthly insurance costs. Another often-overlooked deduction is the cost of any professional development or training you've had to do related to your son's care. Things like CPR certification, specialized autism care training, or workshops on managing behavioral issues can sometimes be deductible as medical expenses if they're directly related to providing necessary care for your son's condition. Keep track of any adaptive technology purchases too - tablets with communication apps, weighted blankets prescribed for sensory needs, or specialized seating can all potentially qualify as medical expenses with proper documentation from healthcare providers. The fact that you're providing 24/7 care really opens up a lot of possibilities for legitimate deductions that many families don't realize they can claim.

California definitely has some great caregiver support programs! You should look into the California Earned Income Tax Credit (CalEITC) and the Young Child Tax Credit - with your income level and dependents, you might qualify for additional state credits beyond the federal ones. For the behavior management course, that $800 should absolutely be deductible as a medical expense with proper documentation. Get a letter from the behavioral therapist stating the training was medically necessary for providing care for your son's autism. The IRS has generally been favorable toward training expenses that are directly related to caring for a dependent's medical condition. One more California-specific tip - check if you qualify for the state's Dependent Care Assistance Program or any regional center services that might provide additional support. Sometimes these programs can help offset expenses that would otherwise come out of pocket, and knowing about them can help with tax planning. Also, since you mentioned weighted blankets and sensory tools, make sure you're documenting the medical necessity for each item. A simple letter from an occupational therapist explaining how each tool addresses specific sensory processing issues related to your son's autism can make all the difference if you're ever questioned about these deductions. The fact that you're keeping such detailed records puts you in a great position to claim everything you're legitimately entitled to!

One thing I haven't seen mentioned yet is the importance of understanding how summer funding might be handled differently. Many grad programs have different funding structures for summer months - sometimes it's research assistant wages (W-2), sometimes it's fellowship money (1099 or no form at all), and sometimes students are on their own to find funding. I learned this the hard way when my summer research stipend was processed as a fellowship rather than wages, which meant no taxes were withheld at all. I ended up with a surprise tax bill the following year because I wasn't prepared for the different treatment. If your son's program has summer funding, I'd recommend asking the graduate program coordinator or financial aid office specifically how summer stipends are classified and reported. This way you can plan ahead for any potential tax differences rather than being caught off guard later. Some students end up needing to make quarterly estimated payments during summer months if taxes aren't being withheld from fellowship-type funding. Also, international students have completely different tax rules that can be even more complex, but I'm assuming your son is a US citizen/resident based on your post. Just wanted to mention it in case it's relevant for anyone else reading this thread!

As someone who's been through this maze myself, I can confirm that the tuition waiver portion should indeed be tax-free since your son is working as a research assistant! The key thing that saved me a lot of headaches was getting everything in writing from the university early on. I'd recommend having your son request a formal letter from the graduate school or financial aid office that breaks down exactly how his funding package is structured - specifically stating the tuition waiver amount and confirming his status as a research assistant. This documentation becomes invaluable if there are ever any questions down the road. Also, since he's in a 5-year program, it's worth noting that some universities change their internal systems or reporting methods over time. I had friends whose funding was reported differently in year 3 versus year 1 of the same program, not because the actual tax treatment changed, but because the university switched payroll systems. Having that baseline documentation helps ensure consistency. One last tip - if your son plans to do any conference presentations or publish research, keep track of any related expenses not covered by the university. These can sometimes be deductible as unreimbursed employee expenses, though the rules changed somewhat with recent tax law updates. Good luck navigating this - you're asking all the right questions!