Is this still true if the LLC owner is on payroll too? Like if they're getting a W-2 from their own company?

No, that changes things significantly. If the LLC owner is receiving a W-2 from the business (putting themselves on payroll), then they're treating the LLC as an S-Corp for tax purposes, not a single-member LLC with pass-through taxation. In that case, the owner's W-2 would have withholding just like any employee, and those withholdings would be credited automatically when you enter the W-2 in TurboTax. The business would still file its own return (typically Form 1120-S for an S-Corp), and the owner would receive a K-1 for their share of profits beyond their salary.

Not the OP but our accountant recommended we switch to S-corp status once our profits hit about $40k annually. The savings on self-employment tax were worth the extra paperwork.

Any recommendations on what income level typically makes it worth claiming? I'm in a similar situation with about $12k in AMT credits but not sure if my $110k salary will trigger enough regular tax to recover anything.

At $110k, you'll likely recover some of your credits, but it depends on your deductions, filing status, and other factors. If you're single with standard deduction, you'd probably begin to recover credits at that income level. Generally, I've found that married couples often need $150k+ combined income before recovering significant AMT credits, while singles can start seeing benefits around $90-100k. Consider consulting with a tax pro for a year-by-year projection based on your specific situation.

If you do a disqualifying disposition (selling before meeting holding requirements), it gets even more complex. The good news is you'll generally receive an AMT income adjustment that can help recover some of your AMT in the year of sale. The bad news is you'll pay ordinary income rates on the spread instead of capital gains rates.

Can you actually switch from MFJ to MFS after you've already filed? I'm in the same boat and wondering if I should amend.

Yes, you can switch from married filing jointly to married filing separately by filing an amended return (Form 1040-X), but only until the filing deadline for that tax year. After the deadline passes, you can't switch from joint to separate. However, my accountant actually advised against switching in our case. While it looked like we'd get refunds filing separately based on a simple calculation, we would have lost several valuable credits and deductions that are only available to joint filers. The separate filing calculation also has some special limitations that aren't obvious when you just run a basic comparison. Make sure you're looking at the complete picture before making that decision.

Is this still true with the new tax law? I thought they changed some of this stuff.

Thanks, that's a good point about state requirements. My situation is actually a bit different from last year since I had a big job change plus the crypto stuff, so I'm not sure if last year's return would be helpful as a baseline. What other approaches would you suggest for estimating?

Since your situation changed significantly with both a job change and crypto, you're right that last year's return might not be as helpful. In that case, I'd suggest doing a quick calculation of your W-2 income and estimated tax liability from that (you can find tax tables online), then add an additional amount for crypto. For the crypto portion, even a rough estimate based on your trading volume would help. If you traded $10,000 in crypto with an average gain of 20%, you might set aside roughly 25-30% of those gains ($500-600) for taxes as a starting point. It's not perfect, but it shows good faith effort.

Same happened to my brother! He trades crypto too and just put $0 on his extension form thinking it was just a time extension. He ended up owing about $4k in taxes plus another $800 in penalties and interest. Definitely better to overestimate.

Yikes, that's exactly what I'm trying to avoid! Did you try calling the IRS to get the penalties removed or reduced? I've heard sometimes they'll work with you if it's your first time making this mistake.

Thanks for breaking it down so clearly! I've never filled out a W-9 before. Is there anything tricky about it that I should watch out for?

The W-9 is actually pretty straightforward. The main things to be careful about: Make sure you're using the current version of the form from IRS.gov - it's occasionally updated. Fill in your legal name (as shown on your tax return), not a business name unless you have one registered. For most independent contractors, you'll check the "Individual/sole proprietor" box. The trickiest part is deciding whether to provide your SSN or an EIN (Employer Identification Number). If you're just working as yourself, your SSN is fine. If you've set up a formal business structure, you might have an EIN to use instead.

This is why I use QuickBooks Self-Employed - it explains all this stuff and tells you what forms you need vs what forms others should give you. Helped me avoid so many headaches with clients who dont understand contractor taxes.