Does anyone know if this is different for LLC vs sole proprietor? I have a single-member LLC but file Schedule C.

This is such a common confusion point for self-employed folks! I went through the exact same thing when I started my consulting business. The key is proper documentation - make sure your invoices clearly separate the reimbursed expenses from your service fees. I use a simple format like "Service Fee: $X, Travel Reimbursement: $Y" on each invoice. This makes it crystal clear to both you and the IRS that these are genuine reimbursements, not additional income. One tip that helped me: I keep a separate spreadsheet tracking each reimbursed expense with the corresponding receipt and invoice number. Makes tax time so much easier and gives you bulletproof documentation if questions ever come up. TurboTax handles this pretty well if you enter everything in the right categories - just make sure you're consistent about how you classify things. The peace of mind of doing it right from the start is definitely worth the extra bookkeeping effort!

One additional angle worth exploring - have you looked into whether your company offers any flexible work arrangement policies that could help reduce these monthly trips? Many employers have started implementing "hybrid work" guidelines that allow employees to substitute some in-person requirements with virtual participation. You might be able to propose attending every other monthly meeting virtually, cutting your hotel costs in half. Also, if your role involves specific tasks that require office access (like equipment, files, or face-to-face collaboration), consider batching multiple months' worth of office work into longer but less frequent visits. Instead of monthly overnight trips, you could potentially do quarterly 2-3 day trips, which might be more cost-effective and easier for your employer to justify reimbursing. The key is presenting it as a business efficiency improvement rather than just a cost-saving request. Show how reducing travel frequency could increase your overall productivity and reduce the company's indirect costs from your travel days.

I've been following this thread closely since I'm dealing with almost the exact same situation - 4-hour commute to our main office for monthly meetings. After reading all the great advice here, I wanted to add something that worked for me: I approached my manager with a "pilot program" proposal rather than asking for permanent policy changes. I suggested a 6-month trial where I'd attend every other monthly meeting virtually, with the understanding that we'd evaluate the impact on team collaboration and my work quality. This approach worked because it gave my manager an easy way to say yes without committing to long-term policy changes. The pilot framing also made it feel innovative rather than like I was trying to get out of work requirements. Six months later, not only did they make it permanent, but they extended the same option to two other remote team members in similar situations. Sometimes companies just need to see that these arrangements can work before they're willing to formalize them. For anyone considering this approach: I made sure to over-communicate during the virtual meetings and volunteered to take on some additional coordination tasks to demonstrate my continued engagement with the team. The key was showing that virtual participation could actually add value, not just maintain the status quo. The cost savings have been significant - I went from 12 hotel nights per year to 6, saving me about $1,200 annually. Not a complete solution, but definitely meaningful relief while I continue to explore the other tax and reimbursement strategies mentioned in this thread.

I've been dealing with this exact same issue! What I ended up doing was creating a simple spreadsheet to track my major purchases throughout the year while waiting for the IRS calculator to be updated. I set up columns for date, store, purchase amount, and sales tax paid. The key insight I learned is that you don't need to track EVERY single purchase - focus on the big ones. Things like appliances, electronics, furniture, car repairs, etc. For day-to-day purchases like groceries and gas, the IRS table estimates are usually pretty close. I also discovered that some credit card companies and banks categorize your spending in their year-end summaries, which can help you identify categories where you might have paid significant sales tax. It's not perfect, but it gave me a good starting point for estimating until the official tools are available.

For anyone still struggling with this, I found a workaround that's been working well for me. Since the IRS calculator isn't updated yet, I've been using the IRS Publication 600 which has the sales tax tables in PDF format. You can download last year's version and manually look up your income bracket and state to get a baseline estimate. The tables are organized by income level and filing status, and then broken down by state and local tax areas. It's a bit more tedious than using the online calculator, but it gives you the same underlying data. You can find it by searching "IRS Publication 600" on the IRS website. Also, if you made any major purchases like a car, boat, or expensive home improvement materials, you can add those actual sales tax amounts on top of the table amount. The instructions in the publication explain exactly how to do this calculation. This method has helped me get a much more accurate estimate for my tax planning while we wait for the 2025 tools to be released.

Has anyone actually tried doing exactly what the original poster is asking about? I'm in an almost identical situation (part-time job, not eligible for their 401k, doing a large Roth conversion), and my tax software flagged my IRA deduction when I entered the Roth conversion amount.

Just wanted to chime in as someone who went through this exact scenario last year! I was part-time at a company with a 401k but wasn't eligible due to hours worked, and I also did a substantial Roth conversion that pushed our income way up. The key insight everyone's mentioned is absolutely correct - your eligibility to participate in your employer's plan is what matters, not whether your employer has one. Since you're not eligible due to part-time status, you're considered "not covered" and can deduct traditional IRA contributions regardless of income level. One practical tip: when you file your taxes, make sure to answer the retirement plan coverage questions carefully. The software will ask if your employer has a retirement plan (yes) but then ask if YOU are eligible to participate (no). Getting this right is crucial for the deduction calculation. Also, keep documentation from your employer showing you're not eligible for the 401k due to part-time status. It's unlikely you'll need it, but it's good backup if questions ever arise about your coverage status. With your $25k in earned income, you'll have plenty to support the full $15k in IRA contributions for both you and your wife. The Roth conversion income actually helps your overall tax planning here since it creates room for the traditional IRA deductions to offset some of that conversion income.

Did you check the envelope the 1099 came in? Sometimes companies print their EIN on the return address or other materials included with the tax form. Also, if this company has ever paid you before, check last year's 1099 if you have it. One other thing to try - if it's a company with a website, sometimes they include their EIN in the footer of their website or on their "About Us" page if they're government contractors or do certain types of business.

If you're still having trouble reaching the company and need to file soon, I'd recommend documenting your attempts to get the correct TIN. Keep records of when you called, emailed, or otherwise tried to contact them. This shows good faith effort on your part. You can absolutely file with "unknown" in the payer TIN field as others have mentioned. The IRS is primarily concerned with accurate income reporting. Just make sure you report the full $5,800 on your Schedule C and include a brief note in your tax software or on paper explaining that you attempted to obtain the payer's TIN but it was not provided on the form. Also, since this is freelance income over $400, don't forget you'll need to pay self-employment tax on this amount in addition to regular income tax. Make sure your tax software is calculating that correctly when you enter the 1099-MISC income.