Doesn't this also depend on whether the medical practice is an S-corp or sole proprietorship? I thought the rules were different.

Just want to add that timing matters a lot here too. Since your sister just purchased the building last year, she needs to be careful about how she handles the transition. If she's been using it for business since purchase, she should have been taking depreciation deductions on her Schedule C already. If she decides to go the separate entity route (like the LLC approach mentioned above), there could be tax implications for transferring the property from personal ownership to the LLC. This might trigger capital gains or other issues depending on how much the property has appreciated. Also, make sure she's aware of the passive activity loss rules if she goes with rental income - these can limit her ability to deduct losses from the rental property against her active medical practice income. The rules are pretty complex and depend on her level of participation in managing the property. Definitely worth getting professional advice before making any structural changes, especially since she's doing well financially. The wrong move could end up costing more than the potential tax savings.

My situation was a little different but might be helpful. My 2017 divorce had both alimony and child support. In 2022, we modified BOTH the child support and alimony amounts because my income changed dramatically. My accountant warned me that because we modified the actual alimony amount after 2018, I lost the grandfather status and can no longer deduct it! So based on my experience, if your modification only touched child support and left alimony completely alone, you should be fine. But if you modified the alimony amount or terms at all, even in the same document as the child support changes, you might have lost the deduction.

This is exactly the kind of complex tax situation where the details really matter. Based on what you've described, since your 2023 modification was specifically for child support (due to your oldest graduating college and youngest changing schools) and your divorce was finalized in 2018, you should still be able to deduct your alimony payments. The key question is whether your modification document touched the alimony terms at all. If it only addressed the child support calculation and left the $2,250 monthly alimony amount and terms completely unchanged, then you maintain your grandfathered status under the pre-2019 rules. However, I'd strongly recommend getting a definitive answer before your quarterly payment deadline. You might want to review your modification paperwork carefully to see if it mentions alimony at all, or consider reaching out to the IRS directly for clarification on your specific situation. The peace of mind of knowing for certain is worth it when you're dealing with $27,000+ annually in deductions.

Has anyone dealt with tax vs book basis issues for accrual to cash conversion? My accounting is on accrual basis (because it makes more sense for our operations) but we file taxes on cash basis. It's becoming a nightmare to convert everything at year end.

One thing I've learned from managing this for my own business is that prevention is better than cure when it comes to book vs tax basis differences. I set up a simple system where I code transactions with tax implications right from the start. For example, when I enter a meal expense, I use a specific account code that reminds me it's only 50% deductible. For equipment purchases, I immediately note whether I plan to use Section 179 or regular depreciation. This way I'm not scrambling at year-end trying to remember the details of every transaction. Also, regarding your sales tax question - think of sales tax collected as "holding money for the government." It never becomes your income, so it should go straight to a liability account. Sales tax you pay becomes part of your expense or inventory cost, which does affect your income taxes as a deduction. The key is keeping good records from day one rather than trying to sort everything out later!

Call the IRS directly if ur unsure about anything. Better safe than sorry

Another telltale sign of this scam is the timing - legitimate EIP payments ended years ago, so any new messages claiming you're eligible for a $1,400 payment should be an immediate red flag. The IRS doesn't send out surprise payments via text, and they definitely don't ask you to "provide accurate personal information" through suspicious links. Always remember: if it sounds too good to be true and comes through an unexpected channel, it probably is a scam.

This isnt directly about Form 8300 but make sure ur keeping good records of the purchase. the hobbyist might call it a "personal collection" but the IRS might view differently depending on their selling history. If they've made multiple big sales the IRS could argue they're actually in business.

Great question about Form 8300! Just to add some clarity - you're correct that you wouldn't need to file Form 8300 in this situation since you're paying by check, not cash. But I wanted to mention something else that might be relevant for your trading card business. If you're regularly buying collections over $10k, you might want to consider whether you need to register as a money services business (MSB) depending on your transaction volume and patterns. It's not common for card dealers, but I've seen cases where high-volume businesses got flagged for not having proper AML (anti-money laundering) procedures in place. Also, make sure you're getting proper documentation for the purchase - receipts, any provenance documentation, photos of high-value items, etc. This protects you if there are ever questions about the legitimacy of the collection or if you need to prove your basis for future sales. The hobbyist angle is interesting too - if they're liquidating a truly personal collection they've held for years, they might qualify for favorable capital gains treatment on their end. Just something to keep in mind if they ask about tax implications of the sale.