Has anyone actually successfully deducted dental implants specifically? My dentist said they might be considered "cosmetic" and not medically necessary even though I literally couldn't eat properly without them.

I went through this exact situation last year with a $7,500 implant after losing a tooth in an accident. Here's what I learned: The IRS considers dental implants medically deductible when they're necessary to restore normal function - eating, speaking, preventing bone loss, etc. The key is having proper documentation from your dentist explaining the medical necessity, not just cosmetic improvement. For your situation with $23k income and a $9k expense, you'd definitely exceed the 7.5% AGI threshold ($1,725), so you could potentially deduct about $7,275. However, as others mentioned, you'd need to itemize to claim this. One thing that helped me was keeping detailed records of ALL related expenses - not just the implant itself, but any preparatory work, follow-up visits, medications, and even mileage to/from dental appointments. These smaller expenses add up and can help push your total itemized deductions closer to making itemizing worthwhile. Also consider if you have other potential itemized deductions like charitable donations, state/local taxes, or student loan interest that combined with the dental expense might make itemizing beneficial overall.

Just adding my experience for others searching: My housekeeper is definitely an independent contractor. She has her own business name "Spotless Spaces", sets her rates, decides which cleaning products to use, and has her own liability insurance. She even has employees of her own sometimes! The IRS would never consider that an employer-employee relationship with me. Don't overthink it - if someone is clearly operating an independent cleaning business with multiple clients, they're a contractor. Just make sure to issue a 1099-NEC if you pay them $600+ in a year. I use tax software that makes this super easy.

I've been dealing with a similar situation and wanted to share what I learned from my tax preparer. The key distinction is whether your housekeeper is operating as a business or working as your personal employee. From what you've described - 20 different clients, setting her own schedule, bringing supplies, and determining methods - she's clearly running her own cleaning business. The IRS looks at the degree of control you have over the worker. If she's making her own business decisions and serving multiple clients, that screams independent contractor. One thing that helped me was keeping records of our arrangement: copies of her business cards if she has them, text messages showing she sets the schedule, receipts showing she buys her own supplies, etc. This documentation supports the independent contractor classification if you ever need to justify it. Don't let the "household employee" rules confuse you - those apply when someone works primarily in your home under your direction. Your housekeeper is running her own enterprise. Just get her W-9 filled out and issue a 1099-NEC if you pay over $600 annually.

Has anyone tried the IRS Direct File program this year? I heard they expanded it to more states for 2025 filing season. Wondering if it works better than dealing with OLT or TurboTax.

This is exactly why I always bookmark the official IRS Free File page (https://www.irs.gov/filing/free-file-do-your-federal-taxes-for-free) at the beginning of tax season. These companies count on people going directly to their commercial websites where they can charge for "premium" features. What's really frustrating is that OLT's marketing emails don't even mention that their completely free version is still available through the IRS portal. They're deliberately steering people toward their paid service. I fell for this exact trick with H&R Block a few years ago before I learned about the Free File program. Pro tip: If you qualify for Free File (AGI under $79,000 for most providers), bookmark that IRS page and ONLY access tax software through those links during filing season. Don't trust the "free" versions on company websites.

This thread has been incredibly helpful! I'm dealing with a similar situation with my father's accounts and the gift tax implications have been keeping me up at night. One thing I wanted to add based on my recent research - the IRS Publication 950 (Introduction to Estate and Gift Taxes) has some specific guidance on joint accounts that might be relevant here. It mentions that when joint account holders contribute different amounts to the account, the tax treatment can get complicated. In your case, since your mom funded the entire account and your sister never contributed her own money, there might be an argument that your sister's "ownership" is really just administrative. However, as others have pointed out, the legal right of survivorship still applies regardless of who contributed what. I'm curious - has anyone here actually been audited on a joint account transfer like this? I keep reading about the theoretical tax implications, but I wonder how often the IRS actually pursues these cases in practice, especially for amounts under $100k. Also, @Mohammed Khan, you mentioned your mom has most assets in the trust already. Have you considered just moving this checking account into the trust as well? I know you wanted to keep it separate for bill-paying convenience, but many banks now offer online trust account management that makes it almost as easy as a regular checking account. That would completely eliminate the gift tax question since distributions would be governed by the trust terms rather than joint ownership rules.

This is a really comprehensive discussion that's been incredibly educational! As someone who works in banking compliance, I wanted to add a few practical considerations that might help with your decision-making process. First, regarding the joint account structure - you're absolutely right to be concerned about the gift tax implications. What I see frequently is families who set up joint accounts for convenience without fully understanding the tax consequences. The "right of survivorship" feature that makes these accounts attractive for avoiding probate is exactly what creates the gift tax issue later. A few additional thoughts: **On POD/TOD designations:** Most banks can convert your existing joint account to have your sister as the primary owner with you as a POD beneficiary. This usually requires minimal paperwork and maintains the convenience factor while eliminating the gift tax concern. **On trust accounts:** The online banking concern is becoming less of an issue. Most major banks now offer the same digital services for trust accounts as regular accounts. The main difference is slightly more paperwork for large transactions, but for routine bill paying, it's virtually identical. **On documentation:** Even if you stick with the current structure, having a contemporaneous written statement from your mom about her intentions is crucial. I'd recommend something more formal than a handwritten note - perhaps a brief letter typed and signed in the presence of a witness, stating that the account funds should be divided equally between her children upon her death. **Timing consideration:** If you do end up in a situation where your sister needs to file Form 709, remember that the gift tax return is due by April 15th of the year following the gift. Don't wait until the following tax season to figure this out. The peace of mind from restructuring the account now is probably worth any minor inconvenience. These situations are stressful enough without adding tax complications on top of everything else.

Has anyone used Drake Tax software to report this kind of situation? I'm trying to figure out the best way to enter the grant as non-taxable and handle the M-1 adjustments in Drake, but the software seems to get confused when I try to create the deferred revenue portion.

For S-Corp grant reporting, the key is understanding whether you have a performance obligation. If the grant requires specific activities or expenditures, only recognize income as you fulfill those obligations - this keeps the unused portion as deferred revenue on your balance sheet. Here's what I'd recommend for your 1120-S: 1. If the entire grant is truly non-taxable and has no performance requirements, include it in book income and back it out on M-1 Line 5 as "Income recorded on books this year not included on return." 2. If there are performance obligations for the unused portion, treat only the "earned" portion as current income, with the remainder as deferred revenue. This approach is cleaner for multi-year situations. 3. Make sure your grant agreement clearly states the tax treatment - some grants are explicitly non-taxable while others might create taxable income depending on how funds are used. The documentation is crucial here. Keep detailed records of how you determined the taxable vs non-taxable portions, especially if the grant has specific use restrictions. This will be important if you face any questions later from the IRS or state tax authorities. What type of grant did you receive? The specific nature (research, PPP forgiveness, state economic development, etc.) can impact the exact treatment required.