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Omar Farouk
Don't forget about your state taxes too! Even if you can deduct the interest on your federal return, state rules vary widely. For example, my state doesn't allow investment interest deductions at all, while some states follow federal rules.
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?
Omar Farouk
ā¢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.
Chloe Davis
How did you determine the interest rate for your family loan? I'm thinking of doing something similar, but I'm not sure what rate would be considered "reasonable" by the IRS.
AstroAlpha
ā¢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.
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StarStrider
With your situation, I'd strongly consider a mid-tier EA (Enrolled Agent) rather than a CPA. I was in almost the exact same boat last year - ISO options, rental property, ESPP. Found an EA who specializes in tech workers for $600 total. CPAs are often overkill for personal returns unless you have business ownership or extremely complex investments. EAs focus specifically on taxation and often charge less than CPAs while having plenty of expertise for situations like yours. Plus they have unlimited representation rights with the IRS if anything comes up later.
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.
StarStrider
ā¢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.
Zara Malik
Just wanted to throw another option into the mix. I tried FreeTaxUSA last year for a similar situation (RSUs instead of ISOs, but also had a rental property). It was only $15 for the premium version and handled everything perfectly. TurboTax wanted to charge me $200+ for essentially the same service. The interface isn't as polished but it asks all the same questions and handles AMT calculations. If you're willing to learn a bit as you mentioned, you might be surprised how capable the budget options are these days.
Luca Marino
ā¢Does FreeTaxUSA handle multi-state returns well? I have property in one state but live in another like OP.
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Paolo Rizzo
Anyone have good experiences with H&R Block? Thinking about trying them next year after using TaxAct for years.
Amina Sy
ā¢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.
Paolo Rizzo
ā¢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.
I've filed with both Jackson Hewitt and H&R Block, and personally found Block to be marginally better, but neither was great for my situation with rental properties and self-employment income. Ended up switching to a local CPA who charges $400 but has saved me thousands in deductions the big chains missed. Sometimes you get what you pay for.
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.
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Just wanted to add that if the gymnastics academy is a 501(c)(3) specifically (not all nonprofits are - there are different types of 501c organizations), they could potentially set up a scholarship or general travel fund that people could donate to directly. This would make the donations tax-deductible while still supporting the team's travel. The important distinction is that donors cannot earmark their contributions for specific students. The nonprofit must maintain control over how the funds are used, even if they end up using them for your team's trip.
Kelsey Chin
ā¢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.
One option nobody has mentioned - could the instructor invoice the academy directly for the international competition, and then you make donations directly to the academy's general fund (not earmarked)? Then the academy could choose to allocate those funds to pay the instructor for the competition. The key difference is the money flow and who has control. If donors give to the academy's general operating fund with no strings attached, those could be deductible. Then it's the academy's decision how to use those funds.
Nathan Dell
ā¢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.
Ahooker-Equator
My mortgage company does this too! The 1099-INT on the mortgage statement is typically interest they paid you for having excess funds in your escrow account. If you overpaid into escrow during the year, that money earned a tiny bit of interest, which they're required to report. The other 1099-INT is probably for your checking/savings accounts. Two completely different interest payments, but both taxable and need to be reported separately.
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Anderson Prospero
ā¢Is the bank required by law to pay interest on escrow accounts? My escrow account has thousands in it and I've never seen a 1099-INT attached to my mortgage statement.
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Ahooker-Equator
ā¢It varies by state. Some states have laws requiring mortgage servicers to pay interest on escrow accounts (California, Connecticut, Maine, Maryland, Massachusetts, Minnesota, New Hampshire, New York, Oregon, Rhode Island, Utah, Vermont, and Wisconsin). In other states, it's up to the terms of your mortgage agreement. If you live in one of those states and have a significant escrow balance but never received interest, you might want to check with your mortgage servicer. It's possible the interest was so minimal they didn't need to report it (usually under $10), or there could be specific exemptions in your state's laws.
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Tyrone Hill
Something nobody mentioned yet - double-check if the 1099-INT on your mortgage statement has a different account number in Box 3 compared to your regular 1099-INT. This would confirm they're for different accounts (likely your escrow account vs checking account). Also, you should verify the bank's tax ID number (EIN) on both forms - it should be the same since it's the same bank. If they're different, that could indicate the forms are from different entities within the bank's corporate structure.
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Toot-n-Mighty
ā¢This is good advice. I had a similar situation with Chase last year and the account numbers in Box 3 were different. One was for my savings account and the other was for escrow interest.
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