Good point! I completely forgot to consider state tax implications. I'm in California - any idea if they allow investment interest deductions similarly to the federal rules?

California generally conforms to federal treatment of investment interest expense deductions. So if you can deduct it on your federal Schedule A, you should be able to deduct it on your California Schedule CA (540), assuming you're itemizing on both returns. Just make sure all your documentation is solid since family transactions get extra scrutiny from both the IRS and the California Franchise Tax Board. The loan should absolutely have a reasonable interest rate and formal payment schedule.

The IRS publishes the Applicable Federal Rates (AFR) monthly, which are the minimum interest rates they consider legitimate for loans. You can Google "IRS AFR rates" to find the current ones. They have different rates for short-term, mid-term, and long-term loans. If you charge less than the AFR, the IRS might consider part of the loan as a gift, which creates a whole different tax situation. For family loans for investments, it's usually safest to use the exact AFR rate or slightly above it.

I hadn't even considered an EA! How did you find one who specializes in tech compensation? That price point sounds much more reasonable than what the CPAs are quoting.

I found mine through the National Association of Enrolled Agents website (naea.org) - they have a directory where you can search by specialty. I filtered for ones who listed "equity compensation" as a specialty. Many EAs who work with tech employees advertise their familiarity with ISOs, RSUs, ESPPs, and startup equity. Some even offer free initial consultations where you can discuss your situation before committing. I'd look for someone who has experience with both rental properties and equity compensation specifically. The sweet spot for your situation is definitely an EA who has tech industry experience but doesn't charge CPA rates.

Does FreeTaxUSA handle multi-state returns well? I have property in one state but live in another like OP.

I used H&R Block for 3 years until I realized I was paying $250 for them to enter information I could do myself. Their software is decent but the in-person preparers vary WILDLY in quality. I had one who was amazing (former accountant) and two who clearly just completed their basic training course. One missed a major education credit I was eligible for until I specifically asked about it.

Thanks for the honest feedback. That's what I was worried about - paying a premium for someone who just plugs numbers into the same software I could use myself. Maybe I'll just upgrade my TaxAct subscription instead of switching to in-person prep.

How did you find your CPA? I've been thinking about switching to one but don't know where to start looking for someone reliable.

I asked other small business owners in my area for recommendations. Personal referrals are usually the best way to find a good CPA. Another good approach is to check with your state's CPA association - they often have directories of members organized by specialty. I interviewed three before choosing mine, asking about their experience with rental properties and small business taxes specifically.

That's a great idea! Do you know if there's a way to check what specific type of nonprofit they are? Their website just says "nonprofit organization" but doesn't specify the 501c classification.

You can look up their tax-exempt status using the IRS Tax Exempt Organization Search tool at https://apps.irs.gov/app/eos/. Just enter the organization's name or EIN number. You could also just ask the organization directly - they should know their tax status. If they're a 501(c)(3), they're eligible to receive tax-deductible contributions. If they're another type of 501(c) organization (like a 501(c)(7) social club), then donations wouldn't be deductible even if made directly to them.

This is actually a gray area that could get the nonprofit in trouble. If there's an understanding that donations to the "general fund" are actually intended to pay for specific students' expenses, the IRS could consider it a disguised payment for services rather than a donation. The nonprofit could risk their tax-exempt status if they're facilitating this type of arrangement.

I've been claiming depreciation each year, but I'm not sure I understand how the recapture works. Do I pay 25% on the total amount I've claimed in depreciation over the years? And is there any way to reduce this tax hit?

Yes, you'll pay 25% on all the depreciation you've claimed (or were required to claim even if you didn't). It's separate from your capital gains tax and is reported on Form 4797. One way to potentially defer both capital gains and depreciation recapture tax is by doing a 1031 exchange into another investment property. But that only works if you want to stay in real estate investing, not if you're cashing out. There are strict timelines though - you need to identify potential replacement properties within 45 days of selling and complete the purchase within 180 days. You also need to use a qualified intermediary to hold the funds. Not simple, but it can save a ton in taxes if you're staying in the real estate game.

Replacing carpet is generally considered a repair as long as you're not upgrading substantially. So if you're replacing worn carpet with similar quality carpet, that would be a repair expense you can deduct on Schedule E this year rather than adding to basis.