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Don't forget to check if you qualify for the Qualified Business Income Deduction (QBI) with your Schedule C businesses! That's a potential 20% deduction on your qualified business income. That might explain why the tax website is showing you owe so much - if you didn't account for that deduction.
Thank you for mentioning QBI! I didn't even know about that deduction. Do both of my businesses qualify for that? And would I apply it to each Schedule C separately?
Yes, both of your businesses should qualify for the QBI deduction as they're both reported on Schedule C. The deduction is actually calculated on your total qualified business income across all qualifying businesses, not on each Schedule C separately. The basic calculation is 20% of your net business income (after expenses), but there are income thresholds where it starts to phase out or get more complicated (over $170,700 for single filers in 2024, which doesn't sound like it applies to you). This deduction alone could significantly reduce what you owe, possibly explaining the high amount you saw on the first website you tried.
When I had two Schedule Cs, I found it helpful to use tax software specifically designed for self-employed people rather than the free options. The extra $50-60 was worth it for the guidance on splitting expenses and proper documentation.
After using both systems, I will say the one advantage TurboTax has is the W-2 and 1099 import feature. I have like 8 different 1099-B forms from my brokerage and manually entering all those transactions in FreeTaxUSA was a giant pain. TurboTax just pulled them all in automatically. But if you don't have a ton of forms or complicated investments, FreeTaxUSA is definitely the better value. Just my 2 cents.
Do you know if Cash App Tax has import features? I've heard mixed things but thinking about trying it this year.
Cash App Tax does have some import capabilities, but not as extensive as TurboTax. Last I checked, they could import W-2s by taking a picture, and they can import some 1099s from major brokerages like Robinhood and a few others. The coverage isn't nearly as comprehensive as TurboTax though, which can connect to hundreds of financial institutions. If you have accounts at smaller or less common brokerages, you might still need to enter things manually with Cash App Tax.
I used H&R Block for years until I realized I was paying $120+ for them to enter numbers from my W-2 into a computer... something I could literally do myself in 20 minutes lol. Switched to FreeTaxUSA and saved so much!!
The free versions often miss deductions though. My cousin works for H&R Block and says they train them to upsell because the free version is designed to be incomplete.
Something to check - did your benefits change at all during this transition? Sometimes when companies switch payroll systems, there are subtle changes to how pretax deductions are handled (like health insurance, 401k, HSA, etc). This can make a big difference in your taxable income and withholding. Also, if you live in a state with income tax, make sure both state and federal withholdings look correct. I've seen cases where the new system got federal right but completely messed up state withholding calculations.
Thanks for the suggestion! My health insurance premium did actually increase slightly during this period, but the pretax deduction amount seems correct. I'll definitely double-check my state withholding though - I hadn't even thought to look at that separately! I'm in Minnesota, and now that you mention it, the state withholding does look a bit different on the new paystubs compared to federal. I'll compare the percentages to make sure everything adds up.
Has anyone suggested just talking to your payroll department directly? When my company switched from ADP to Workday last year, there were a bunch of withholding issues. Turns out they had imported some of the employee data incorrectly. When I showed them my old vs new paystubs, they fixed it immediately. Could save you a lot of trouble!
This is good advice. I work in HR and I can tell you we WANT to know about these issues. Sometimes during system migrations, default settings get applied instead of employee-specific ones. We can't fix what we don't know about!
Just to add a slightly different perspective - make sure you're considering the potential returns on that money too. If your investment is returning 8% but your loan interest is 6%, it might make sense to keep the loan and not pay it off early since you're net positive. But if the market turns and your investments start losing value while you're still paying (or accumulating) interest, that leverage works against you. I've been burned by this before when I had too much margin during a market downturn.
That's a really good point! My investment return has been about 11% annually while my loan interest is around 7%, so I've been ahead so far. But you're right about the risk - a market downturn could flip this equation quickly. Are there any strategies you use now to protect against that kind of scenario?
I maintain a much lower margin percentage now - never more than 20% of my total portfolio value. This gives me enough cushion to withstand even a severe market correction without facing a margin call. I also set up automatic alerts to notify me when my margin utilization crosses certain thresholds. This helps me stay proactive rather than reactive. And I keep a portion of my portfolio in less volatile investments that can provide stability during market turbulence - this has saved me several times when tech stocks took a nosedive.
Has anyone actually used Schedule A for investment interest deductions recently? With the standard deduction being so high now ($13,850 for singles in 2023), it seems like most people wouldn't itemize anyway, making this whole discussion moot for many investors.
Investment interest expense doesn't go on Schedule A anymore - it goes on Form 4952 and then the deductible amount transfers to Schedule A. But your point about the standard deduction is valid. For me, between state/local taxes, mortgage interest, and charitable contributions, I'm already itemizing, so investment interest deductions are definitely worthwhile. But if you're not already over the standard deduction threshold, you're right that this strategy might not matter much.
Thanks for the Form 4952 clarification - shows how long it's been since I've done this! I wasn't aware of the form change. You make a good point about already itemizing for other reasons. I forget that in high-tax states or with large mortgages, many people easily exceed the standard deduction. I'm in a no-income-tax state with a paid-off house, so I rarely have enough deductions to itemize anymore.
Ella Russell
Quick question - do S-Corps still get the 20% pass-through deduction (QBI) like sole props do? I heard something about income limits and wasn't sure if S-Corps have different rules for that.
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Mohammed Khan
•Yes, S-Corps are eligible for the 20% Qualified Business Income deduction. The same income thresholds apply ($170,050 for single filers and $340,100 for joint filers in 2025). Above those thresholds, limitations based on W-2 wages and qualified property start to phase in. Actually, this is where S-Corps can have an advantage over sole props for high earners. Since you're paying yourself a W-2 salary, that can help you qualify for larger QBI deductions if you're over the income threshold. It's a bit complicated but basically your W-2 wages to yourself can help satisfy the wage limitation tests.
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Gavin King
S-Corps are awesome but no one talks about how the IRS scrutinizes them more. My friend got audited specifically because he took too much in distributions compared to salary. They reclassified a bunch of his distributions as wages retroactively and he owed a ton in back taxes + penalties. Make sure your salary vs distribution split can pass the smell test!
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