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I've been a tax preparer for 10+ years and the premium deduction question confuses a lot of clients. Here's a quick breakdown of what's deductible: Self-employed? Health/dental/vision/LTC premiums = fully deductible as adjustment to income Not self-employed? Only as itemized medical expense (if >7.5% of AGI) Business owner? Liability/malpractice/etc = business expense Homeowner? Homeowners insurance = NOT deductible for personal residence Long-term care = partially deductible based on age brackets The problem with tax software is they often ask these questions in different places based on your answers to earlier questions. That's probably why you're seeing it in FreeTaxUSA but not TurboTax.
What about Medicare premiums? I'm retired but also have some self-employment income from consulting. Are those deductible too? TurboTax never seems to ask me about this.
Medicare premiums (Parts B and D) are indeed deductible as part of the self-employed health insurance deduction if you have self-employment income! This is a commonly missed deduction. The key is that you can only deduct premiums up to the amount of your net self-employment income. If you're using TurboTax, you'll need to look in the self-employment section and find where you enter your health insurance. There should be an option to include Medicare premiums there. If your consulting income is reasonably substantial, this could be a significant tax savings for you.
Random question but has anyone tried the IRS Free File program instead of commercial software? I'm wondering if it handles these premium deductions more clearly. I'm so tired of discovering that I've been missing deductions for years because of how tax software presents questions.
I used IRS Free File through one of their partners last year and it was actually pretty straightforward about insurance premiums. It specifically asked about self-employed health insurance in a separate section and had clear explanations. Much more direct than the commercial versions where they hide things in weird places.
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Some important nuances your relatives should consider regarding the S-Corp situation: 1. If they keep the S-Corp but change the main business activity from operating a business to holding rental property, they need to be careful about the "passive investment income" rules. S-Corps that previously operated active businesses but switch to primarily generating passive income (like rent) can face additional taxes if they have accumulated earnings and profits from C corporation years. 2. They should also consider whether keeping the S-Corp structure makes sense for rental property. There are often better entities for holding rental real estate, like an LLC taxed as a partnership or even direct ownership, depending on liability concerns and their specific situation. 3. The "step transaction doctrine" would likely apply if they create an LLC, buy property, then have the S-Corp buy it right after the asset sale. The IRS might treat it as a single transaction and disallow 1031 treatment.
This is super helpful. They've had the S-Corp for about 20 years, and it was always an S-Corp (never a C-Corp), so maybe the passive income concern isn't an issue? Do you think it would be better for them to just dissolve the S-Corp after the asset sale and create a new LLC specifically for the rental property? Or would that trigger immediate taxation on the asset sale proceeds?
You're right that the passive income concern wouldn't apply if they've always been an S-Corp, so that's good news. That issue primarily affects companies that converted from C to S status. Creating a new LLC after dissolving the S-Corp could be a better long-term solution. However, the dissolution would still trigger taxation on the asset sale proceeds - you can't avoid that tax by changing entities afterward. The tax is due when the sale occurs while still in the S-Corp. If they're set on the rental property approach, they might consider selling the business assets, distributing the after-tax proceeds to themselves personally, and then purchasing the rental property in their own names or through a new LLC. This gives them a clean break from the business entity and often provides better tax treatment for rental properties, especially regarding potential future benefits like step-up in basis for heirs.
Just to clear up some confusion about 1031 exchanges specifically - there are two key points that would make this challenging: 1. The "held for investment" requirement: The property being sold must be held for investment purposes or used in a trade or business. While their business property likely qualifies, changing the use from business operations to rental income might be problematic. The IRS looks at intent, and they might question whether the original property was truly "held for investment." 2. Timing issues: A 1031 exchange requires you to first sell your property, then acquire the replacement property within specific timeframes. You can't acquire the replacement property first (which is what the LLC scenario would be attempting to do). The reverse 1031 exchange does exist, which allows buying the new property before selling the old one, but it's complex and requires a specialized Exchange Accommodation Titleholder to temporarily hold title to one of the properties.
Would the reverse 1031 exchange work in their situation? I'm curious because I'm facing a similar issue where I need to acquire a new property before my current one sells.
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Have you looked into the Credit Karma Tax platform (now called Cash App Taxes)? It's completely free for federal and state filing, even with complex returns. I switched from TurboTax to them two years ago and haven't looked back. It's not fully forms-based like you're asking for, but it gives you much more flexibility to jump between sections without forcing you through the entire interview process again. And you can't beat the price - FREE.
I've heard mixed things about Cash App Taxes - doesn't it have limitations on which forms it supports? I need to file some investment forms and I think I read somewhere that they don't support all of them. Have you used it with any complex investing situations?
You're right that it does have some limitations. It works for most common investment forms (1099-B, 1099-DIV, etc.), but doesn't support some of the more obscure forms. I have fairly standard investments and it worked fine for me. They don't support foreign income, multiple state filings, or K-1 forms for partnerships. If you need any of those, it wouldn't work for your situation. Their website has a complete list of supported forms that's worth checking against your specific needs before you invest time in entering all your data.
For California residents, don't forget about CalFile! It's the state's free e-filing system for CA state taxes. Obviously doesn't help with federal, but at least you can save money on the state portion. I combine CalFile for my state return with a cheaper option like FreeTaxUSA for federal. That way I'm only paying for one return instead of two.
CalFile is great but they have income limits and other restrictions. Worth checking if you qualify first: https://www.ftb.ca.gov/file/ways-to-file/online/calfile/qualifications.html Not everyone will be eligible unfortunately!
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Another free option to consider is Cash App Taxes (formerly Credit Karma Tax). I've used it for the past three years and it handles capital gains/losses, including carryovers. Completely free for federal and state regardless of complexity. The only major limitations are that it doesn't support multiple state filing, foreign income, or undistributed long-term capital gains. But for most college students it's perfect.
Does Cash App Taxes handle 1099-MISC forms? I did some freelance design work and got one of those, plus I have some investment stuff to report.
Yes, Cash App Taxes handles 1099-MISC forms without any issues. I've used it for freelance income alongside investment reporting for years now. The interface for entering 1099 information is actually pretty straightforward, and they support multiple 1099s if you had several clients. They also walk you through any deductible expenses related to your freelance work, which can significantly reduce your taxable income from those gigs.
I was in the exact same boat last year! Had to report stock losses and TurboTax wanted $120 for their premium package. Switched to FreeTaxUSA and paid $0 instead of $120. One tip for anyone with investment stuff: gather ALL your documents before starting. My 1099-B had substituted cost basis info that confused me and I had to start over. But even with that hassle, FreeTaxUSA was way better than paying TurboTax's ransom fee lol.
Whats substituted cost basis mean? I have investments but im confused by all the tax language on my forms.
Dmitri Volkov
I think we're overlooking the psychological aspect of taxation. With a progressive system, people generally understand that as they earn more, they'll pay a higher percentage. It feels intuitive to most. A flat tax creates a situation where someone earning $40k pays the same rate as someone earning $4 million. While mathematically the wealthy person pays more in absolute dollars, it doesn't account for the diminishing utility of money as wealth increases. Also, removing ALL exemptions would create weird situations. Would charitable donations no longer be deductible? Would businesses not be able to deduct legitimate expenses? That seems untenable.
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Sasha Ivanov
•You make a good point about the psychological aspect. I hadn't considered that angle before. But regarding business expenses - couldn't those be handled separately from personal taxation? Like keep business deductions but simplify personal taxes? And for charitable giving, I wonder if people would still donate without the tax incentive...
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Dmitri Volkov
•That's a really interesting question about separating business and personal tax structures. It could work in theory, but then you'd still need a complex system for business taxation. Most economists think there should be symmetry between personal and business tax structures to prevent gaming the system. As for charitable giving, studies have shown that tax incentives do influence donation behavior significantly. While people would still give to causes they care about, the research suggests overall giving would decrease by 25-40% if the deduction was eliminated. This would hit smaller local charities the hardest since they rely more on middle-class donors who are more tax-sensitive.
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Tyrone Johnson
I'm confused about smthg... if we had a flat tax with NO exemptions whatsoever, wouldn't that mean even people on social security and disability would get taxed? That seems really harsh. And what about people working minimum wage jobs? They're already struggling to make ends meet.
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Ingrid Larsson
•A well-designed flat tax would still have a basic exemption amount. So maybe the first $25,000 or $30,000 isn't taxed at all, then everything above that is taxed at a single rate like 15% or 20%. That would protect low-income earners while simplifying the rest of the system.
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