Has anyone used TurboTax for this scenario? I'm wondering if it handles this situation correctly or if I should go to a professional preparer this year.

I went through this exact same situation last year and it was really confusing at first! You absolutely need to file Schedule H even though your payroll service is making the estimated payments. Here's what I learned: The Schedule H shows the IRS that you had household employment tax obligations, while the 1040-ES payments you already made get credited toward your total tax liability. Think of it this way - Schedule H calculates what you owe, and the estimated payments show what you've already paid toward that debt. Your payroll service should provide you with a year-end summary showing total wages paid, Social Security, Medicare, and federal unemployment taxes. Use those exact numbers on Schedule H. The estimated tax payments you made throughout the year will appear as credits on your 1040, so you won't pay twice. One tip: double-check that the total of your quarterly estimated payments matches (or comes close to) the total household employment taxes shown on Schedule H. If there's a big discrepancy, you might need to make an additional payment or expect a refund. I was terrified of messing this up, but once I understood that Schedule H is just reporting what happened (not creating a new tax bill), it made much more sense!

As someone who works in the entertainment industry (background acting and some commercial work), I've dealt with similar questions about appearance-related deductions. One thing that hasn't been mentioned yet is the "but for" test - would you have gotten the veneers "but for" your modeling work? Since your agent specifically recommended this and you have documentation showing increased bookings, that's a strong argument for business necessity. I'd also suggest keeping track of any maintenance costs for the veneers that are specifically related to your modeling work - like touch-ups before big shoots or cleaning appointments timed around bookings. These ongoing costs might be easier to defend as pure business expenses. Another angle to consider: some models I know have had success writing off a percentage based on the proportion of their income from modeling versus other sources. So if 60% of your income comes from modeling, you might be able to justify deducting 60% of the veneers cost. The documentation you have sounds solid - agent emails and booking rate increases are exactly what you'd need if questioned. Just make sure you have clear records of your income before and after the procedure to quantify that business impact.

I work as a tax advisor and have dealt with several cases involving appearance-related deductions for models and actors. While this is definitely a gray area, you actually have some strong documentation that could support your case. The key factors working in your favor are: 1) Your agent's specific recommendation (this is crucial evidence), 2) The measurable increase in bookings after the procedure, and 3) The direct connection between your appearance and income in modeling. However, be prepared for potential IRS scrutiny. Cosmetic dental work is often viewed as having significant personal benefit since you retain the improved appearance 24/7. To strengthen your position, I'd recommend: - Documenting the exact percentage increase in your modeling income post-veneers - Keeping all communications from your agent about this recommendation - Consider deducting only the portion that's proportional to your modeling income vs. total income Given that this is a substantial expense ($10,500) and potentially audit-triggering, I'd strongly suggest consulting with a tax professional who has experience with entertainment industry deductions before filing. They can help you present the strongest possible case and ensure you're following all the proper documentation requirements. The good news is that with your level of documentation, this isn't automatically disallowed - it just needs to be handled carefully and professionally.

Be careful with some of these approaches. I tried using the Taxpayer Advocate Service (TAS) route last month during peak filing season, and they've implemented strict case acceptance criteria. Their Internal Revenue Manual (IRM) section 13.1.7.2 specifically prohibits TAS from accepting cases where the taxpayer is simply trying to circumvent normal IRS channels. If your issue doesn't meet their definition of 'significant hardship' under IRC section 7811, you'll be redirected back to the main IRS queue with wasted time.

Last year I had a similar business tax issue and discovered that the IRS Practitioner Priority Service line (866-860-4259) can sometimes be more effective. They typically serve tax professionals, but I've found that if you're prepared, knowledgeable about your issue, and have all your business documentation ready, they often will assist you directly. I was transferred three times but eventually reached someone who resolved my S-Corp filing issue in one call. The key difference from my previous attempts was calling mid-week around 2pm Eastern time.

Has anyone used the TurboTax live expert feature for this kind of situation? I'm having a similar issue and wondering if it's worth the extra cost or if they just tell you generic advice you could find online.

I went through something very similar when I converted my home to a rental property mid-year. The 15-day rule is indeed frustrating, but don't worry - your expenses aren't lost! Here's what I learned after consulting with my CPA: Those $6k in expenses you mentioned are considered "startup costs" for your rental business. Since you didn't rent for 15+ days in 2023, you're right to delete the rental from your 2023 return per the software's guidance. For 2024, when you're actively renting, you have a few options: 1. Add all expenses to your property's basis and depreciate over 27.5 years 2. Make a Section 195 election to deduct up to $5,000 in startup expenses immediately in your first year of business, with the remainder amortized over 15 years The second option could be huge for you since you have $6k in expenses. You'd deduct $5k immediately in 2024 and spread the remaining $1k over 15 years. Make sure to categorize your expenses correctly between repairs (potentially immediately deductible once rental activity begins) versus improvements (must be capitalized). Keep detailed records of everything with receipts and descriptions. The key is that your rental business officially starts in 2024, not 2023, so that's when these rules kick in. Don't let the software trick you into thinking you've lost those deductions forever!

Just wanted to add that this mistake happens more often than you'd think. My broker did something similar last year when I transferred securities between accounts. They lost the original purchase date and reported everything as if I'd bought the shares the day they arrived in the new account. Make sure you check ALL your 1099-B forms carefully, especially if you: - Transferred securities between brokerages - Had any corporate actions (stock splits, mergers, etc.) - Participated in dividend reinvestment plans - Made wash sales These scenarios often cause reporting errors on 1099-Bs.

This is exactly why I always keep my own detailed records of all stock purchases and sales, completely separate from what my brokerage reports. I use a simple spreadsheet with purchase dates, amounts, and prices for every transaction. When situations like this come up, I have my own documentation to back up the correct information. It's saved me multiple times when brokers made errors on 1099-B forms. I'd recommend everyone do this going forward - don't rely solely on your brokerage's record-keeping. For your current situation, definitely pursue this aggressively. The tax difference between short-term and long-term treatment on a substantial NVIDIA gain could be thousands of dollars. If you have any old account statements, email confirmations, or even bank records showing the original purchase in December 2020, use those to support your correction on Form 8949.