Something else to consider - if your businesses grow significantly, you might want to restructure into separate LLCs for liability protection. I started like you with multiple businesses under one EIN as a sole prop, but after my Amazon business took off, I formed an LLC for that part to protect my personal assets. You can still use pass-through taxation with an LLC (Schedule C), but you get better protection if something goes wrong with one business. The other businesses wouldn't be affected.

One thing I'd add from my experience running multiple businesses under one EIN - make sure you're prepared for potential complications if you ever need to apply for business loans or credit. Some lenders get confused when they see multiple business activities under a single EIN, especially if the revenue streams are very different like yours (real estate, e-commerce, subscription service). I had to provide extra documentation to explain how my different businesses operated when I applied for a business line of credit. It wasn't a dealbreaker, but it did slow down the approval process. Just something to keep in mind as your businesses grow. The tax side works fine with one EIN as others have mentioned, but the banking/lending side can sometimes be trickier.

Has anyone dealt with using retirement funds to purchase overseas property? I'm considering using some of my IRA to buy a place in Spain but heard this might be considered a prohibited transaction and trigger massive penalties.

This thread has been incredibly helpful! I'm in a similar situation planning to buy property in Portugal next year. One thing I haven't seen mentioned is the timing of when you need to file these forms. From what I've researched, the FBAR is due by April 15th (with an automatic extension to October 15th), but Form 8938 is filed with your regular tax return. Is there any benefit to timing the property purchase at a certain point in the tax year to make reporting easier? Also, does anyone know if there are different requirements if you're buying the property as a primary residence versus an investment property? I'm planning to eventually retire there but initially it would be a vacation home that I might rent out occasionally.

I got audited on charitable contributions 2 years ago and learned the hard way. For donations under $250 you need either a receipt from the org OR bank records + some evidence of donation. For donations over $250, you MUST have written acknowledgment from the charity - no exceptions. Pictures help but aren't sufficient by themselves. Your best move is getting that acknowledgment letter now and keeping whatever receipts you have. For items without receipts, you can estimate fair market value but be reasonable - the IRS has seen every trick in the book.

Great advice from everyone here! As someone who's dealt with similar documentation issues, I'd add that when you contact the shelter for that acknowledgment letter, offer to draft it yourself with all the details and just ask them to review and sign it. This makes their job easier and ensures you get exactly what you need for IRS purposes. Also, for future donations like this, consider taking a quick video as you're packing everything - it can serve as great documentation of both the items and your charitable intent. And definitely get that receipt at drop-off time! One more tip: if you do get questioned later, having photos of the assembled packages plus the shelter's social media posts showing your donation creates a nice paper trail that supports your story. The IRS appreciates when donations have logical documentation that tells a coherent story.

Just to make sure you've considered everything - have you calculated whether the medical expense deduction actually justifies filing separately? Remember that medical expenses are only deductible to the extent they exceed 7.5% of your AGI. Filing separately often increases your overall tax burden in other ways.

Great question! I went through something very similar last year. The nominee recipient approach is definitely your best bet here, and it's more straightforward than it sounds. A few practical tips from my experience: First, make sure you split the gains proportionally based on how you actually funded the account (50/50 if you contributed equally, or whatever the actual split was). Second, when you file the nominee 1099-B, include a clear statement with both returns explaining the situation - something like "Capital gains from joint brokerage account reported under [your SSN] but income split per actual ownership." One thing to watch out for - if you have any capital loss carryforwards from previous years, those stay with whoever originally claimed them and can't be transferred to your spouse's return. This might affect your overall calculation. Given the $1,200+ potential savings others calculated, it's definitely worth doing. The IRS sees nominee situations regularly, especially with married couples filing separately, so as long as your paperwork is clear and consistent, you shouldn't have any issues.

Has anyone dealt with social security after a parent passes? My dad was getting monthly checks and one came after he died. Not sure if I need to return it or report it somewhere on taxes??

Sorry for your loss. Yes, you can absolutely still claim your mom as a dependent for 2024 even though she passed away in April. The IRS allows you to claim someone as a dependent for the entire tax year if they met the dependency requirements during the time they were alive. Since you were supporting her, she lived with you, and her income was minimal (just Social Security), she would qualify as your dependent. Make sure to keep good records of the support you provided - housing, food, medical expenses, etc. You'll also want to have her death certificate on hand in case the IRS ever asks for documentation. One thing to also consider - any medical expenses you paid for her care can potentially be included in your medical expense deductions if you itemize. Those final months often involve significant medical costs that you might be able to deduct.