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Need advice on tax service options for more complex tax situation - stock options, rental property, etc.

My wife and I have been using a budget tax preparer (around $350) for the past few years, but our 2024 taxes are getting more complicated and I don't think our current guy is up to the task. We're trying to figure out our best option moving forward. I'm wondering if it makes sense to try handling it myself with software like TurboTax, maybe with their expert guidance feature? Or would going to H&R Block or Jackson Hewitt ($350-$500 range) be worth it because they might catch things I'd miss? Local CPAs in our area (Baltimore) want to charge almost $1,400 for federal and state returns, which seems excessive compared to the national chains. Here's what's making our tax situation more complex this year: We're Maryland residents but own a rental property in Ohio that we're planning to sell either this year or next, then move those funds to our investment account. My wife's company went public in early 2024, and her ISO stock options are starting to vest. We understand their value and have plans for which ones to sell this year versus exercising and holding. We're factoring in the alternative minimum tax implications and know the stock sales will bump up our taxable income. We're also enrolled in her company's employee stock purchase program, which lets us buy approximately $35,000 of company stock in December at a 15% discount. Beyond that, things are fairly standard. We file jointly, with my wife's salary of about $220,000 being our only employment income. We have two kids, recently refinanced to a 15-year mortgage, and maintain a brokerage account in the low six figures on top of our retirement accounts. My wife keeps excellent records, and we have copies of our previous returns. Any recommendations on what level of tax help I should seek for our situation? Tax amateur trying to figure out the best approach after what's turning into a complicated tax year.

StarStrider

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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.

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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.

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StarStrider

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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.

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Zara Malik

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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.

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Luca Marino

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

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NeonNomad

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Our family accountant explained it to me as: "Each partner has their own capital account. When the partnership makes money, everyone's account increases based on their ownership percentage. When someone takes money out, only their account decreases." It's really that simple. Just look at Box L on your Schedule K-1 (Form 1065) - it tracks your capital account. The ending capital account should equal: Beginning capital + income allocated to you - distributions to you + any additional contributions you made. For tax planning, remember that distributions aren't taxable unless they exceed your basis. The K-1 income is taxable regardless of whether you receive distributions.

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Does this work the same way for an LLC taxed as a partnership? My LLC's K-1 looks similar but has different codes in some boxes, and I'm confused if distributions work differently than in a traditional partnership.

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NeonNomad

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Yes, it works exactly the same way for an LLC taxed as a partnership. The tax code treats them identically. The K-1 might have different codes depending on the types of income or deductions being allocated, but the basis rules are the same - your basis increases with your share of income and decreases with distributions. The only difference might be in some of the legal aspects or state-specific requirements, but from a federal tax perspective and for basis calculation purposes, an LLC taxed as a partnership follows the same rules as a traditional partnership.

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Quick question related to this - our family partnership just sold a significant asset with a $250K gain. If I get a distribution of $50K (my share of the proceeds), but my K-1 shows $60K of gain allocated to me (my ownership percentage), how does that affect my basis? Does my basis go up by $60K then down by $50K?

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That's exactly right. Your basis would increase by the $60K gain allocated to you on the K-1, and then decrease by the $50K distribution you received. So your net basis change would be a $10K increase.

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Don't forget about depreciation recapture when you sell! Everyone focuses on the capital gains, but the depreciation recapture at 25% can be a nasty surprise if you haven't planned for it. Every year you've owned that rental, you've been taking depreciation (or should have been), and the IRS wants that back upon sale.

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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?

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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.

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Quick question for anyone who might know - I'm replacing carpeting in my rental before selling. Is this a repair (deductible) or improvement (added to basis)? It's just standard carpet, nothing fancy.

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Cass Green

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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.

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Omar Farouk

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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.

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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?

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Omar Farouk

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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.

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Chloe Davis

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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.

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AstroAlpha

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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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Paolo Rizzo

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Anyone have good experiences with H&R Block? Thinking about trying them next year after using TaxAct for years.

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Amina Sy

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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.

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Paolo Rizzo

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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.

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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.

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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.

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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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