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Something nobody's mentioned yet - you might want to consider if S-Corp election for your LLC could help in this situation. As an S-Corp, you could pay yourself a reasonable salary and take the rest as distributions, which aren't subject to self-employment tax. This could potentially lower your MAGI (Modified Adjusted Gross Income) for ACA subsidy purposes while filing jointly with your spouse. It's a bit more complex administratively, but the tax savings can be substantial if your business continues to grow. Obviously talk to a tax pro about whether this makes sense for your specific situation, but it's something to consider as part of the overall strategy.
At what income level does S-Corp election make sense? I've heard different opinions about whether it's worth it when your business makes less than $100k annually. Is there a general rule of thumb?
The general rule of thumb is that S-Corp election starts making financial sense when your net business profit reaches approximately $40,000-$50,000 annually. Below that, the additional costs of running an S-Corp (payroll processing, more complex tax filing, etc.) often outweigh the self-employment tax savings. For ACA subsidy purposes specifically, S-Corp can be beneficial at even lower income levels sometimes, because properly structured salary vs. distributions can optimize your MAGI. But this requires careful planning and consistent profitability, which might be challenging with the variable income described in the original post. Always best to model different scenarios with actual numbers before making this decision.
One thing that helped us was setting up a QSEHRA (Qualified Small Employer Health Reimbursement Arrangement) through my LLC. It allows me to reimburse myself and my spouse tax-free for medical expenses including insurance premiums. We still file jointly to get the marketplace subsidy, but the QSEHRA gives us additional tax benefits. There are some specific rules you have to follow but it's been really helpful for managing our health costs.
I thought QSEHRA was only for businesses with employees? Can you really set one up if you're a single-member LLC with no employees besides yourself?
Ok but one thing nobody's mentioned - what about state taxes? Do states treat qualified dividends and capital gains the same way as federal? I'm in California and they seem to tax everything at the same high rate no matter what.
You're right about California - they don't give preferential treatment to long-term capital gains or qualified dividends. Everything gets taxed at the same rate based on your income bracket. Some states follow federal rules (giving lower rates to long-term gains/qualified dividends), some states have their own preferential rates, and some states like California tax everything the same. It's definitely worth checking your specific state rules.
Random question but does anyone know if tax software like TurboTax handles all this correctly? Like do I need to manually separate out my qualified dividends when entering everything or does it do that automatically?
TurboTax handles this automatically. As long as you enter your 1099-DIV forms correctly (or import them directly from your broker), it will apply the correct tax rates to each type of investment income. Same with H&R Block and most other tax software - they're designed to apply all these different rates correctly. The software is actually pretty good at this part.
I've seen weird stuff in Box 14 for years and usually just ignore it. My last job put "NJSUI" and "NJSDI" there along with some dollar amounts. Turned out it was just New Jersey state unemployment insurance and disability insurance contributions. Totally normal and didn't affect my federal return at all. Your backslash might be a glitch, but honestly unless there's a dollar amount next to it that seems wrong, I wouldn't sweat it. Box 14 is the wild west of W2 forms... employers put all kinds of random stuff there.
Thanks for all the responses everyone! I finally heard back from my company's HR person. Turns out the "\" was indeed a software glitch in their payroll system. They're sending corrected W2s, but she confirmed it doesn't affect any of the tax calculations since there wasn't an amount associated with it. I feel much better now knowing it won't delay my refund. Appreciate all the help!
Small tip for future reference - you can actually ask your employer for a "W-2c" (corrected W-2) if there are errors on your W-2, even for Box 14 issues. Most people don't know employers are required to provide this if there are mistakes. Doesn't sound like you need it now since the backslash doesn't have an amount, but good to know for future tax seasons!
Is there a deadline for requesting a W-2c? I think I might have an error on mine from last year but never followed up on it.
I've been doing taxes for friends with crypto for a few years. One thing nobody mentioned is that transfers between wallets (like from Coinbase to your personal wallet) aren't taxable events - but transfers to a casino ARE considered disposals because you're effectively "selling" your crypto to the casino for gambling credits. That's an important distinction. Also, offshore casinos are a gray area. They technically should report large winnings to the IRS, but many don't. That doesn't absolve you from reporting, though - the responsibility is still on you as the taxpayer.
So given my specific situation - if I buy Bitcoin and immediately transfer to a casino, I'd report it on Form 8949 as a purchase and sale with zero gain/loss? And then the gambling part would be totally separate on different forms?
That's exactly right. You'd show the Bitcoin purchase and disposal on Form 8949 with the same amounts (so zero gain/loss). Then separately, you'd report any gambling winnings on Schedule 1 as "Other Income." If you itemize deductions rather than taking the standard deduction, you could potentially deduct gambling losses (up to the amount of your winnings) on Schedule A. But only if your total itemized deductions exceed the standard deduction, which is $13,850 for single filers in 2023.
Has anyone dealt with the record-keeping nightmare for this? My gambling site only keeps 3 months of history and I've been doing this all year. Should I be taking screenshots of every session? What counts as adequate proof for the IRS?
I use a spreadsheet to track everything - date, amount of crypto purchased, transfer to site, gambling sessions with wins/losses. I also take screenshots of big wins and all withdrawals. For the actual crypto purchases, your exchange should have all that history available to download.
Oliver Fischer
My husband and I went through this last year. Our preparer claimed we had a home business that didn't exist. When we amended, we: 1) Paid the additional tax (about $3,800) 2) Paid interest (around $320) 3) Got hit with a 20% accuracy penalty (~$760) But that was IT. No audit, no criminal investigation, nothing scary. The IRS actually sent us a thank you letter for voluntarily correcting the return. Our CPA said they're mainly concerned with willful fraud, not people fixing honest mistakes.
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Ava Johnson
ā¢Did you have to do anything special when submitting the amended returns? Like explain why you were changing things or attach any documents? I'm worried I'll mess up the amendment process somehow.
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Oliver Fischer
ā¢We included a detailed statement explaining exactly what happened - that we discovered our previous preparer had included false deductions without our knowledge, and we were voluntarily correcting the error as soon as we discovered it. Our CPA advised us to be completely transparent about the situation. We attached documentation showing the correct information for each modified item. The most important part was being clear and thorough about what was being changed and why. Our CPA said this approach often helps avoid deeper scrutiny since it shows good faith. Just make sure your EA documents everything properly and includes a clear explanation of the circumstances.
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Natasha Ivanova
Quick question - does anyone know how long amended returns take to process these days? I filed one back in February and still haven't heard anything.
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NebulaNomad
ā¢I filed an amended return in January and it took almost 5 months to get processed. The IRS website says 16 weeks but that seems optimistic based on what I've seen in tax forums. You can check the status with the "Where's My Amended Return" tool on the IRS website.
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