10 One thing nobody's mentioned yet - you should check if your state has any specific requirements for reporting business ownership transfers. I changed my LLC ownership last year and discovered my state required a separate filing with the Secretary of State within 30 days, completely separate from IRS requirements. Also, if your dad held the S corp for a long time, ask about something called "step-up in basis" possibilities. Depending on how the transfer was structured, this could save you significant taxes down the road.

19 Has anyone here dealt with self-employment taxes when transitioning from employee to owner of an S corp? I'm in a similar situation and confused about whether I should be paying self-employment tax on all business profits now or just my salary portion?

Don't forget that property tax rules can vary by state! In some places, property taxes are paid partly in advance rather than fully in arrears. And some counties have weird fiscal years that don't align with calendar years. Might be worth a quick call to your county tax assessor's office to confirm exactly how your local system works before making any decisions.

Great question! I went through the exact same confusion when I bought my first home. The key thing to remember is that for individual taxpayers, property tax deductions follow the "cash basis" rule - you can only deduct what you actually paid out of pocket to the tax authority in that tax year. Since your escrow account didn't make any property tax payments in 2023, you won't have a property tax deduction for your 2023 return. The credit you received at closing from the seller is considered a purchase price adjustment, not a tax payment by you. When you pay the 2023 property taxes in January 2024 (even though they're for the previous year), that's when you'll get the deduction - on your 2024 tax return that you'll file in 2025. Make sure to keep your closing statement and all escrow records organized, as you'll need them for future reference and when you eventually sell the home.

Just to clarify something that seems to be causing confusion in this thread - there's an important distinction between truly collectible/investment vehicles and regular cars that happen to be a bit special. For a regular car (even if it's a nice classic that you drive on weekends), you generally CANNOT deduct the loss. These are personal-use assets. For cars held EXCLUSIVELY as collectible investments, you potentially CAN deduct losses, but you need extensive documentation showing investment intent. For cars used in a BUSINESS (like a restoration business, car dealer, etc.), losses are generally deductible as business expenses. Most people fall into the first category and can't deduct losses, which is why the general advice is that car losses aren't deductible. Most folks simply can't meet the strict requirements for the exceptions.

This is such a frustrating aspect of the tax code that catches so many people off guard! I went through something similar with a vintage truck I had to sell at a loss during COVID when I needed cash fast. What really helped me understand the situation was learning about the "personal use presumption" - basically, the IRS assumes that unless you can prove otherwise with solid documentation, any vehicle you own is for personal use and enjoyment. Even if you barely drive it, even if it's rare or collectible, the default assumption is personal use. The harsh reality is that the tax code is designed this way intentionally. Personal assets like cars, boats, jewelry, etc. are expected to depreciate as part of their normal use cycle. The IRS views this depreciation as the "cost" of enjoying these items, similar to how you can't deduct the loss when your furniture gets old or your clothes wear out. What I learned from my tax advisor is that if you're serious about treating vehicles as investments going forward, you need to set up that framework BEFORE you buy, not after. This means business entities, proper documentation, storage agreements, maintenance logs, and most importantly - never using them personally. It's a pretty high bar to meet, but it is possible if you're committed to treating it as a true investment rather than a hobby that might make money.

Has anyone actually gotten in trouble with the IRS for incorrectly reporting Box 14 stuff? I've been ignoring most of it for years and just entering the obvious things like union dues. Never had an issue.

I work in tax preparation and can confirm that Box 14 confusion is super common! Your hospital employer is likely using those multiple "HSA EE" entries to track your Health Savings Account contributions by quarter or pay period - this is actually helpful for their recordkeeping. The good news is that HSA employee contributions are pre-tax, so they reduce your taxable income (which is already reflected in your other W2 boxes). When you enter this into TurboTax, it will recognize these codes and handle them appropriately. The software is pretty good at distinguishing between items that need to be reported versus those that are just informational. For healthcare workers, I commonly see Box 14 items like continuing education reimbursements, uniform allowances, parking benefits, and various insurance premiums - most don't require separate reporting on your federal return. Don't stress too much about it - as long as you enter the information accurately as it appears on your W2, you'll be fine!

One important thing no one has mentioned - check if your company offers any tax preparation services or reimbursement for partners! Many partnerships, especially larger ones operating in multiple states, will either provide tax prep services or give you an allowance toward preparing your return. When I became a partner, I found out our firm had negotiated reduced rates with several accounting firms that specialize in our industry. I ended up paying about half what I would have otherwise. It's worth asking your HR or partner resources department about this before you start paying out of pocket.

Another option to consider is hybrid approach - use TurboTax or similar software for the federal return and basic state filing, but consult with a CPA just for the multi-state complications. Many CPAs will do a consultation for $200-400 to review your specific situation and advise you on which states actually require separate filings versus composite returns. I did this my first year with K1 income from multiple states. The CPA confirmed that most of my potential state filings were unnecessary due to composite returns, but identified 2 states where I did need to file separately. They also gave me a roadmap for handling it myself in future years. It was a good middle ground between full DIY (risky) and full professional prep (expensive). Also worth noting - if your partnership income is relatively small compared to your total income, some states have minimum thresholds below which you don't need to file at all, even as a non-resident. A quick consultation can identify these situations and potentially save you from unnecessary filings.