This is such a frustrating situation that so many remote workers are dealing with! I went through the same thing last year when my company suddenly decided that working from home 3 days a week meant I couldn't claim mileage for client visits anymore. What really helped me was putting together a clear timeline showing that my home office arrangement was officially established by my employer, not just something I decided on my own. I included emails where my manager confirmed my hybrid schedule, any home office equipment they provided, and documentation of the regular work I do from home. The IRS is pretty clear that if your employer has established your home as a regular work location (which yours has by officially allowing you to work remotely 3 days a week), then travel from there to temporary work locations like client sites is business mileage, not commuting. The key word is "temporary" - if you're visiting different client sites rather than going to the same location every day, that strengthens your case. I'd suggest creating a simple presentation for your boss showing: 1) Your official remote work arrangement, 2) The varying client locations you visit, 3) The relevant IRS guidance on home-based workplaces. Sometimes employers just need to see it laid out clearly to understand they're interpreting the rules incorrectly.

This thread has been incredibly helpful! I'm dealing with the exact same issue where my employer is claiming that since I work from home, any travel to client sites is considered "commuting" and not reimbursable. One thing I wanted to add that might help others - I found that documenting the *business necessity* of each client visit really strengthened my case. I started keeping a log that included not just the mileage and destination, but also the specific business purpose (client meeting, project site visit, equipment delivery, etc.) and who requested/approved each visit. When I presented this to HR along with the IRS guidance that others have mentioned, it became much harder for them to argue that these were personal commuting expenses. The documentation showed that these weren't routine trips to a fixed workplace, but legitimate business travel to serve different clients at varying locations. I think the key is showing that your situation fits the IRS definition of travel between work locations rather than home-to-office commuting. The more specific you can be about the business nature of each trip, the stronger your case becomes.

What futures broker are you using? I'm getting wrecked by the tax reporting from my current broker. Their 1099s are a nightmare and don't clearly separate section 1256 contracts.

Great question about futures taxation! I've been trading futures for a few years now and can confirm what others have said about the 60/40 rule. One thing I'd add is that you should also consider the wash sale rules, which work differently for futures compared to stocks. With futures contracts under Section 1256, wash sales don't apply the same way they do for securities. This means you can actually realize losses for tax purposes even if you immediately re-enter a similar position, which can be helpful for tax planning throughout the year. Also, since you're projecting such significant profits, you might want to look into making estimated quarterly tax payments to avoid underpayment penalties. The IRS generally wants you to pay as you go, especially with income this large. You can use Form 1040ES to calculate and make these payments. One last tip - keep detailed records of all your trading activity, including timestamps, contract specifications, and P&L for each trade. The IRS can be pretty strict about substantiating trading income, especially at higher amounts. Having clean records will save you headaches if you ever get audited.

I'm dealing with a very similar situation - got promoted to a field service role last year and I'm putting about 25,000 miles annually on my personal vehicle visiting client sites. Like you, my company covers gas but nothing else. After reading through all these responses, I'm realizing I've been leaving money on the table. I had no idea about the state tax deduction possibilities! I'm in Ohio and now I need to research whether we allow unreimbursed employee business expenses on state returns. One thing that's helped me is using a GPS-based mileage tracker that automatically logs my trips. I set it to detect when I'm driving during work hours, and it creates a detailed log with addresses, times, and distances. This has been invaluable for building my case with management. The depreciation calculation someone mentioned earlier really opened my eyes. I looked up my 2022 Honda Civic on KBB - the difference in trade-in value between 12,000 miles (normal annual driving) and 25,000 miles is about $2,800. That's just depreciation, not including the accelerated maintenance schedule I'm now on. I'm planning to compile all these numbers and request a meeting with HR next month. Having concrete data about the true cost of using personal vehicles for business seems to be the key to getting employers to take these requests seriously.

I've been following this thread closely as someone who went through a similar situation with extensive work travel. One thing I haven't seen mentioned yet is the potential insurance implications of using your personal vehicle so heavily for business purposes. When I was driving 20,000+ miles annually for work, I discovered that my personal auto insurance might not fully cover me during business travel if I got into an accident. I had to contact my insurance company to add business use coverage, which increased my premium by about $400 annually - another cost my employer wasn't covering. Also, regarding the state tax deductions people have mentioned - while states like PA, NY, CA, and OH do allow these deductions, the documentation requirements are strict. The IRS and state tax agencies expect contemporaneous records, meaning you need to log your mileage when the trips happen, not reconstruct them months later from memory or credit card receipts. I'd strongly recommend Connor start tracking immediately using one of the GPS apps mentioned, and also have a conversation with his insurance agent to make sure he's properly covered for business use. The last thing you want is to discover coverage gaps after an accident during a work trip. The combination of proper documentation, understanding your true costs (including insurance), and knowing your state tax options gives you much stronger negotiating position with your employer.

LLC vs S-Corp doesnt matter for medicaid its all about your AGI. Go with LLC since your income isnt high enough for S corp to make sense. S corps are a pain with the extra paperwork and payroll requirements!!! An accountant will charge you like $1200+ just for s-corp tax returns. Make sure your tracking all your business expenses properly to lower your AGI. Home office, internet, phone, mileage, insurance, equipment. Every $1000 in legit deductions could be the difference in qualifying or not.

As someone who went through this exact situation two years ago, I can confirm what others have said - your business structure won't help with Medicaid eligibility at your income level. I was making around $30k with my freelance writing business and spent way too much time researching S-Corps thinking it would somehow help with healthcare costs. The reality is that at $28k annually, you're likely well within the Medicaid income limits for expanded states (usually around 138% of federal poverty level, which is about $20,120 for a single person in 2024). Your Modified Adjusted Gross Income is what matters, and that includes your net self-employment income regardless of business structure. My advice: stick with sole proprietorship or form a simple LLC for liability protection if needed. Focus your energy on properly tracking deductible business expenses - that's what will actually lower your MAGI. Things like your home office percentage, business use of your phone/internet, professional development courses, and business equipment can all reduce your taxable income. I wasted months overthinking the business structure when I should have just applied for Medicaid sooner. The application process was much simpler than I expected, and I qualified easily with similar income to yours.

Check if you might qualify for the IRS Fresh Start program too. It helps people who owe back taxes with payment plans and might even reduce penalties. I owed about $3k from 2016 and was able to set up a monthly payment plan of just $85. The most important thing is to be proactive and contact them before they start more aggressive collection actions.

I went through something very similar with a 2016 tax debt that I discovered years later. That transcript format can be really confusing at first! The key thing to understand is that your original debt was $2,750.35, but it's now grown to over $3,700 with interest and penalties. Here's what I'd recommend based on my experience: First, call the IRS to get your current balance since that transcript is from 2022 and more interest has accumulated. Second, ask about penalty abatement options - you might qualify for first-time penalty abatement if you had clean tax history before 2017. Third, don't panic about paying it all at once - the IRS offers payment plans even for older debts. The most important thing is to address this proactively. I waited too long and ended up with a tax lien that took months to resolve. But once I called and set up a payment plan, the stress went away and I was able to handle it with manageable monthly payments. You've got options, so don't let the anxiety overwhelm you!