Does anybody know if the "undetermined term" status affects the actual tax rate you pay? Or is it just an issue of which form/section to report it on? My broker labeled a bunch of my crypto transactions this way and I'm trying to figure out if it actually matters for how much tax I owe or just for paperwork purposes.

I've dealt with this exact situation and want to emphasize something important: when you have undetermined term transactions, the IRS expects you to make a reasonable effort to determine the actual holding period rather than just defaulting to short-term treatment. Here's my recommended approach: First, gather any records you can find - old statements, trade confirmations, even bank records showing when funds were transferred for purchases. Second, if you're missing some information, create a spreadsheet documenting what you know and your methodology for estimates. Third, when in doubt, consider using Form 8949 with the appropriate adjustment codes to explain your situation. One thing I learned the hard way: if you report everything as short-term just because it's "undetermined," you might overpay taxes significantly. The IRS won't refund the difference if you later find records showing they were actually long-term holdings. It's worth spending the time upfront to get this right, especially given the substantial difference in tax rates between short-term and long-term capital gains. Also, keep detailed records of your research process in case of questions later. The IRS appreciates good faith efforts to comply accurately.

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.

Does anyone know if there's a good tax software that makes calculating these estimated payments easier? I've been using TurboTax but it doesn't seem to have a good way to project for the upcoming year or help me figure out these quarterly amounts.

I've been dealing with estimated taxes for years as a small business owner, and I think there's another important point that hasn't been mentioned yet. The IRS actually gives you some flexibility with the safe harbor rules that can make this whole process less stressful. If you pay either 90% of this year's tax liability OR 100% of last year's tax liability (110% if your AGI was over $150,000) through withholding and estimated payments, you won't face underpayment penalties - even if you end up owing more when you file. This means you can use last year's tax return as a baseline for your quarterly payments, which is especially helpful if your income varies significantly. For the uneven quarterly periods, I've found it easier to just set up automatic payments for the same amount each quarter based on last year's taxes. It's not perfectly optimized, but it keeps me safe from penalties and I can adjust when I file my return. Sometimes the peace of mind is worth paying a little extra during the year.

Does anyone know if the rules are different for residential rental property vs commercial? I have both and it seems like there might be different thresholds or rules for each type.

Great discussion here! I'm dealing with a similar situation but with a twist - I have a duplex where I live in one unit and rent out the other. How does the personal vs business use percentage affect these decisions? If I do a $2,000 improvement that benefits both units equally, can I still use the de minimis safe harbor for the 50% business portion? Or does the mixed-use nature of the property complicate things? I've been going back and forth on whether to expense what I can immediately or add everything to basis for when I eventually move out and rent both units. Also wondering if anyone has experience with how this plays out when you convert a personal residence to rental property - do prior improvements suddenly become depreciable at that point?

Great thread! I'm dealing with a similar situation and wanted to add another perspective. I've been running my consulting business as an S Corp for 3 years now, and about 60% of my 1099s come in my personal name despite having an LLC. One thing I'd emphasize that hasn't been mentioned much - make sure you're issuing yourself W-2 wages from your S Corp! This is a requirement that some people miss. The IRS expects S Corp owners who work in the business to pay themselves a "reasonable salary" through payroll before taking distributions. For a $68k contract like the original poster mentioned, you'd probably need to pay yourself at least $30-40k in W-2 wages. Also, regarding the documentation everyone's talking about - I create a simple spreadsheet each year showing all my 1099 income sources, which ones were issued to my personal name vs business name, and how they're reported on my S Corp return. My CPA loves having this because it makes the tax prep much smoother. The self-employment tax savings are definitely worth it if you're making good money, but make sure you factor in the payroll processing costs and additional tax prep fees when doing your calculations.

This is such a helpful discussion! I'm in a similar boat with my consulting LLC and have been hesitant to elect S Corp status because of the 1099 name issue. Reading through everyone's experiences gives me confidence that it's definitely doable. One question I haven't seen addressed - has anyone had issues with state taxes when doing this? I'm in California and know they have their own quirky rules sometimes. Also wondering about quarterly estimated tax payments - do you make them from your personal account for the S Corp taxes or from the business account? The reasonable salary discussion is eye-opening too. I was focused on the self-employment tax savings but hadn't fully calculated in the payroll processing costs and extra complexity. Sounds like it's still worth it for higher income levels, but definitely need to run the numbers carefully. Thanks everyone for sharing your real-world experiences - this is way more useful than the generic advice you find on most tax websites!