I've used both over the years. My CPA handles my normal taxes, business filings, and helps with planning. Only needed a tax attorney once when I got hit with an incorrect $42k IRS bill for unreported income (was actually my ex-wife's but they came after me). Attorney cost more but had the expertise for that specific legal situation. If you're just trying to get your taxes done right and plan properly, start with a CPA. If the IRS is threatening liens, levies, or criminal charges, then you need an attorney. A good CPA will tell you when it's time to bring in legal help.

Having dealt with both CPAs and tax attorneys, I'd recommend starting with a CPA for your situation. Small business and rental income complications are exactly what CPAs handle daily - they'll help you structure your deductions properly and identify any potential audit red flags before they become problems. The key is finding a CPA who specializes in small business taxation rather than just individual returns. They can set up proper bookkeeping systems, advise on business structure (LLC vs S-Corp, etc.), and handle the rental property depreciation correctly. This proactive approach often prevents the issues that would require a tax attorney later. Tax attorneys are definitely worth their fees when you're facing IRS enforcement actions, potential criminal issues, or complex estate/trust matters. But for maximizing deductions and staying compliant with business/rental income, a good CPA will save you money and keep you out of trouble. If problems do arise later, your CPA can work with a tax attorney as needed.

Something nobody's mentioned yet is that if you make under $73,000, you can use the IRS Free File program to access premium tax software for FREE. The software companies hide this option but are required to offer it. Go through the IRS website directly (https://www.irs.gov/filing/free-file-do-your-federal-taxes-for-free) instead of the tax software sites. I used to pay $89 for TurboTax Deluxe plus $49 for state filing, but now I get the exact same software completely free through this program. The income limit increases slightly each year too.

I switched from TurboTax to FreeTaxUSA two years ago and haven't looked back. The interface took a little getting used to at first, but it handles everything I need including my rental property income and business expenses. What really sold me was the price - I went from paying around $150 total (federal + state) with TurboTax to about $25 with FreeTaxUSA. One thing I'd recommend is starting your return early with whatever software you choose so you have time to compare. Most platforms let you input all your info and see the results before you actually pay and file. That way you can test drive a few options and see which interface you prefer and if the refund amounts are comparable. For your side business, make sure whichever software you pick has good guidance on Schedule C deductions. That's where you can really save money if you're tracking business expenses properly - things like mileage, supplies, equipment, even a portion of your phone bill if you use it for business.

Anyone recommend a good tax software that handles rental property sales well? I tried TurboTax last year and it totally messed up my depreciation recapture calculations.

I went through a similar situation last year and learned some hard lessons about capital gains planning. While you can't directly offset the gains from your sold property with improvements to other properties, there are still some strategies worth considering for your current situation. First, make sure you're properly accounting for all the capital improvements you made to the property you just sold - these should increase your basis and reduce your taxable gain. Things like major renovations, roof replacement, HVAC systems, etc. can all be added to your cost basis. For your other properties, those improvements you're planning ($7,800 for flooring, $9,200 for the deck) will still benefit you tax-wise through depreciation over time. Just make sure to keep detailed records and receipts for everything. One thing to consider: if you have other investments showing losses this year, you might be able to harvest some capital losses to offset your rental property gains. Also, depending on your income level, you might qualify for the 0% capital gains rate on a portion of your gain. The tax code around rental properties is complex, so it might be worth consulting with a tax professional who specializes in real estate to make sure you're not missing any legitimate strategies for your specific situation.

Don't forget that for some assets like real estate, you can often get historical appraisals done retroactively. We had a commercial property in my parents' trust, and we hired an appraiser who specialized in retrospective valuations to determine what it was worth when my dad died 9 years ago.

One thing that hasn't been mentioned yet is the importance of getting a Form 706 (United States Estate Tax Return) if one was filed for either parent. Even if the estate wasn't large enough to require filing, many attorneys recommend filing anyway specifically to establish the stepped-up basis values for inherited assets. If a Form 706 was filed for your father in 2016, it would contain the fair market valuations of all his assets as of his date of death - this becomes your stepped-up basis documentation. The same applies for your mother's estate in 2023. These forms are incredibly valuable for exactly the situation you're describing. If no Form 706 was filed, you might still be able to file a protective election or late-filed return in some circumstances. This is definitely something to discuss with a tax professional, as the rules can be complex and there are time limitations involved.

Has anyone tried the alternative of using the individual QBI worksheet for each business but then going into the calculation worksheet form and manually overriding the QBI amount? That's what I've been doing, but I'm not sure if it's the "official" approach that ProSeries recommends.

I've been dealing with this same QBI aggregation headache in ProSeries for the past two seasons. What's worked best for me is a hybrid approach combining several of the methods mentioned here. First, I complete each business activity separately in their respective forms (Schedule C, E, etc.) to get the base QBI calculations. Then I use the QBI calculation worksheet override feature to input the aggregated amount, but I also create a comprehensive supporting statement that includes: - The specific election under Reg. 1.199A-4(b)(1) - Detailed business descriptions and how they meet common control/ownership tests - A reconciliation table showing individual vs. aggregated QBI amounts - Clear documentation that this is a software limitation workaround, not a substantive tax position The key insight I've learned is that the IRS doesn't care how your software handles the calculation as long as your tax position is correct and well-documented. I attach this as a PDF statement through the Forms menu, and it e-files without issues. I've had about 15 clients use this approach over two years with zero problems. The documentation takes maybe 30 minutes to prepare once you have a template, which beats the alternative of paper filing or switching software entirely.