Do they handle Schedule C for small businesses? I have a side hustle selling crafts online and I'm trying to file properly without spending a fortune.

Yes, they do handle Schedule C for small businesses and side hustles. I actually started using them when I had a small consulting gig on the side. It covers all the common business deductions and expenses. The interface for business income isn't quite as polished as TurboTax's, but again, completely free is hard to beat. If you have inventory for your crafts business though, just be aware you'll need to understand the basics of how to track that yourself - this is true of most DIY tax software.

That's interesting - I've always been hesitant about the cost of a CPA, but I never thought about the year-round advice aspect. How did you find your CPA? And did you interview multiple people before choosing?

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.

Yikes, that's exactly what I'm worried about. He's suggesting we file jointly but says he can't pay me his portion until he gets his tax refund from a previous year that's still processing. Did you find that you lost a lot of tax benefits by filing separately? I'm worried about losing my education credits.

That's a huge red flag! If he's waiting on a prior year refund, there's a good chance the IRS is holding it for some reason - maybe prior tax debt, child support, or other government debt. That refund he's counting on might never arrive or might be much smaller than he expects. I did lose some tax benefits filing separately. The biggest hits were lower thresholds for certain deductions and credits and losing the ability to contribute to a Roth IRA (my income was too high for separate filing but would have qualified under joint). However, my education credits actually worked out better filing separately because they have income limits that are easier to stay under with just my income. In your case, with a significant income difference and you being a student, filing separately might actually preserve more of your education credits. The American Opportunity Credit and Lifetime Learning Credit both start phasing out at lower combined income levels.

This is super helpful! One more thing to add - if you file separately and your spouse itemizes deductions, you CANNOT claim the standard deduction. My ex itemized without telling me, and I had to redo my whole return. Also, the income threshold for education credits drops dramatically for married filing separately - I think it's around $10,000 for some credits, which might be below your income.

That's a really good point I hadn't considered. Do you think the mortgage company would report that information directly to the IRS though? Or would they only discover it if they specifically investigated him for some reason?

Mortgage companies don't routinely report down payment sources directly to the IRS - that's not their job. However, they do file what's called a Mortgage Interest Statement (Form 1098) that shows the IRS your friend bought a property. If the IRS ever decides to audit your friend, they'd look at his income versus his expenses and assets. A $50K down payment that doesn't align with reported income would raise immediate questions. The IRS could then subpoena the mortgage application documents, which would reveal the source of funds. It's not about the mortgage company reporting him - it's about the paper trail created during the mortgage process that could be discovered during an audit. The bigger issue is your friend deliberately hiding taxable income, which has no statute of limitations for fraud.

What was the small exchange you used? Was it US-based? I'm wondering if offshore exchanges report to the IRS too or if they're safer.