One thing nobody's mentioned - if your business doesn't end up getting off the ground, those expenses become personal losses subject to the hobby loss rules, which are WAY less favorable. The IRS could argue it was never a real business if you don't eventually show profit motive. Document everything with a clear business plan showing how you expect to become profitable!

Great question! I went through something similar with my consulting LLC last year. A few key points that really helped me: 1. **Separate everything immediately** - Even without income, open a business bank account and get a business credit card. This creates a clear paper trail and protects your personal assets. 2. **The "active business" test is crucial** - You don't need income, but you need to show you're actively trying to generate it. Having your website live, marketing materials ready, or even just being available to take on clients can qualify. 3. **Track EVERYTHING** - I use a simple spreadsheet with columns for date, amount, vendor, category, and business purpose. Take photos of receipts immediately. 4. **Consider your election timing** - You can actually choose when your tax year starts for a new LLC, which might help optimize when you claim those startup deductions. The partnership return (Form 1065) is required even with zero income if you had expenses, but the losses flow through to your personal returns where they can offset other income. Don't wait until you have revenue - getting your systems set up now will save you major headaches later!

Have you considered a Cash Balance plan? With your income level, it might be worth looking into. It's a type of defined benefit plan that could allow you to contribute significantly more than a Solo 401k, especially if you're a bit older and trying to catch up on retirement savings.

Speaking from experience as a self-employed photographer with similar income - don't overlook a backdoor Roth IRA in addition to whatever main retirement plan you choose. I max out my Solo 401k first but also do the backdoor Roth for that tax-free growth. The contribution is small compared to what you can put in a Solo 401k but the long-term tax benefits are huge.

I'd recommend a slightly different approach that worked for me. Instead of selling the same stock in both accounts, consider selling the taxable account position for the tax loss, then immediately exchanging the IRA position for something different but similar (like a competitor in the same industry). This way you're not holding the "substantially identical" security in your IRA anymore, which should allow you to claim the tax loss. And since there are no tax consequences for selling at a loss in the IRA anyway, you're not giving anything up. Just make sure whatever you exchange into isn't considered "substantially identical" to the original security. This approach let me harvest the tax loss without being completely out of the market for 31 days.

This is a really common situation that catches a lot of people off guard! You're absolutely right to be concerned about the wash sale implications. Unfortunately, since you purchased the same stock in your IRA on January 15th (just 7 days after your taxable account purchase), selling the taxable position on February 18th would indeed trigger a disallowed wash sale. The IRS looks at all your accounts - including retirement accounts - when applying the wash sale rule. Here's what I'd suggest: If you want to claim the tax loss, you'll need to sell both positions and wait at least 31 days before repurchasing the same stock in either account. Since you mentioned the stock isn't recovering anyway, this might actually work in your favor from an investment perspective. One thing to keep in mind - your broker's 1099-B will likely NOT flag this as a wash sale because most brokers only track wash sales within the same account. It's your responsibility to identify and properly adjust for cross-account wash sales when filing your return. If you're looking to stay invested in the same sector, consider selling both positions and immediately buying a similar but not identical stock (like a competitor or sector ETF) to avoid being completely out of the market during the 31-day waiting period.

Has anyone else had issues with the IRS questioning their physical presence test documentation when splitting the 330 days across two calendar years? I did something similar last year and the IRS sent me a letter requesting additional proof beyond my travel records.

Great question about the FEIE and differential pay! As someone who's navigated similar military tax situations, I can confirm that your differential pay should qualify for the Foreign Earned Income Exclusion as long as you meet the physical presence test. A few key points to consider: 1. **Timing flexibility**: You don't need to complete all 330 days in 2023. You can use any consecutive 12-month period, so starting mid-February 2023 and going through mid-February 2024 could work perfectly for your situation. 2. **Documentation is crucial**: Keep detailed records of every day you're outside the US - deployment orders, passport stamps, travel receipts, etc. The IRS can be thorough when reviewing FEIE claims, especially for military personnel with complex situations. 3. **Coordinate with your employer**: Make sure your civilian employer understands how they should be handling withholding on your differential pay. Some companies automatically adjust for FEIE, others don't. 4. **Consider state taxes**: Don't forget that some states don't recognize the FEIE, so you might owe state taxes even if the income is federally exempt. The proration calculation across tax years can get complex, so you might want to consult with a tax professional who specializes in military situations to make sure you're maximizing your benefits correctly.

Your employer royally messed up here. Don't let them off the hook. They took your money without consent and that's not ok. Make them refund every cent plus any tax implications. This happened to my sister and she ended up getting almost $2000 back.

This is a frustrating situation that unfortunately happens more often than it should. Here's what I'd recommend based on similar cases I've seen: **Immediate steps:** 1. Document everything - save all your pay stubs, the 1095-C form, and any communication with HR 2. Request a meeting with HR in writing and ask for copies of ANY enrollment forms with your signature 3. If they can't produce signed enrollment documents, you have a strong case for getting your money back **Tax implications:** Since the 1095-C shows you had coverage and premiums were deducted pre-tax, this affects your taxable income. You'll need corrected forms (W-2 and 1095-C) if they reverse the enrollment, which could impact your tax return. **Legal considerations:** Most states require explicit written consent for payroll deductions beyond taxes and court-ordered garnishments. Auto-enrollment policies must be clearly communicated with opt-out procedures. If you can prove you never consented and they didn't follow proper procedures, this could be considered unauthorized wage deduction. Don't let them brush this off - $1,700 is significant money and you're entitled to every penny back if you never authorized the deductions.