That's a good suggestion. There's a senior manager who seems approachable - maybe I could ask her if she'd be willing to do quick pre-reviews for me on the more complex returns. Did you find your mentor within your firm or through a professional organization?

I found my mentor within my firm initially, but I also connected with another experienced expatriate tax professional through our local CPA society's international tax committee. Professional organizations like that are goldmines for finding people who are willing to help. My in-firm mentor would spend 15 minutes with me before I submitted anything complex, which cut my review notes down dramatically. The external mentor was great for bigger-picture career advice. Don't underestimate how willing people are to help someone who shows genuine interest in improving!

The IRS actually has some decent webinars specifically about international taxation. There's also a certification program through the American Academy of Attorney-CPAs focused on international tax that goes into much greater depth than regular CPE.

Thanks for this perspective. I'm worried the IRS might see it that way too. Do you think I should consult with a tax attorney before selling? I'm concerned about potential penalties beyond just calculating the basis wrong.

Consulting with a tax attorney would definitely be a good idea in your situation. They can review the specific details of your transfers and advise you not just on the correct basis calculation but also on any potential exposure you might have regarding the transfers themselves. A good tax attorney can also help you understand the statute of limitations that might apply to your situation and develop a strategy for how to properly document and report the sale to minimize your risk of problems down the road. The peace of mind alone is probably worth the consultation fee.

That's a really good point. For transfers of real estate without consideration, you're supposed to file a Form 709 (Gift Tax Return) even if no gift tax is owed because of the lifetime exemption. If those weren't filed, that could be another issue to address.

But don't you get hit with franchise taxes in most states when you set up those LLCs? I heard California charges $800 minimum per LLC, so with multiple properties that adds up fast. Are the tax benefits really worth those extra costs?

You're right about the franchise taxes - they definitely cut into the benefits. In California it's $800 per LLC which is painful, but I'm in Tennessee where the annual fee is much lower ($300). For me, the math still works out when I consider both the tax advantages and the asset protection. I'm able to legitimately deduct more business expenses through the holding company structure, including a portion of travel related to property management, home office expenses, and administrative costs that were harder to claim as an individual investor.

This is a great question about QBI and holding companies. The Section 199A deduction can be tricky with holding companies because certain structures might limit your ability to claim it. If your holding company is classified as a specified service trade or business (SSTB) and your income is above the threshold (which at $310k, yours is), you'll face limitations. However, a properly structured holding company might allow you to separate SSTB income from non-SSTB income, potentially preserving some of the QBI deduction.

Thanks for mentioning this! Do you know if setting up a payment plan affects your credit score? And is there a minimum amount I have to pay monthly or can I set it to whatever I can afford?

Setting up an IRS payment plan generally doesn't directly affect your credit score - the IRS doesn't report to credit bureaus like a normal lender would. However, if you fail to pay and the IRS files a tax lien, that WILL hurt your credit. So the payment plan actually helps protect your credit by preventing more serious collection actions. For monthly payment amounts, it depends on how much you owe. For debts under $10,000, you can pretty much set your own monthly payment as long as you can pay off the full amount within 3 years. For larger amounts, the IRS may want financial information to determine what you can afford. They're surprisingly reasonable about this - they'd rather get paid slowly than not at all.

This is actually brilliant advice. I had a similar situation (though not as old) and the Social Security earnings record was spot on. Combined with the IRS transcript it gave me everything I needed!

Thanks for the suggestion! Do you know if bank-to-bank transfers also fall under this $600 reporting threshold, or is that just for payment apps?

Bank-to-bank transfers don't fall under the same $600 reporting requirements that apply to payment apps. Those rules specifically target third-party payment networks like PayPal, Venmo, etc. Regular transfers between bank accounts aren't subject to 1099-K reporting regardless of the amount. This is why some people prefer setting up direct transfers for recurring payments like rent or mortgage sharing. It's more straightforward from a tax perspective since there's no confusion about whether it's a business or personal transaction.

That's called "structuring" and it's actually illegal if you're doing it specifically to avoid reporting requirements. Not worth the risk just to avoid something that isn't even taxable in the first place.

Thanks for the info! Definitely don't want to do anything sketchy. Seems like the simplest approach is just to properly mark the payments as personal and not worry about it.