I've been through this exact situation before! Your original plan is absolutely correct - you can print Copy B (contractor copies) on regular paper from the IRS PDF and send them while traveling. The special red scannable paper is only required for Copy A that goes to the IRS. I think your CPA might be confused because he's used to handling the entire 1099 process at once. When you're splitting it up (contractor copies now, IRS filing later), the rules are different. A few practical tips from my experience: - Download the 1099-MISC PDF directly from irs.gov - Fill it out completely and print copies B and C on regular white paper - Keep detailed records of when you sent them (email delivery receipts if sending electronically) - Your CPA can handle Copy A and Form 1096 on the special paper when he files The January 31 deadline is for getting copies to your contractors, which you can absolutely meet with regular paper or electronic delivery. The IRS filing deadline is later anyway (end of February if filing on paper, end of March if e-filing). You're not doing anything wrong - this is a completely legitimate approach that many businesses use when traveling or dealing with timing constraints.

Just to add another perspective from someone who's been handling 1099s for small businesses for years - you're absolutely on the right track with your plan. The confusion often comes from CPAs who are used to handling everything in one batch, but splitting the process like you're doing is perfectly legal and actually pretty common. One thing I'd suggest: when you email or mail the contractor copies, include a brief note explaining that this is their official 1099-MISC for tax purposes, even though it's printed on regular paper. Some contractors get confused when they receive a "plain paper" 1099 instead of the fancy red forms they might expect. Also, make sure you're using the current year's 1099-MISC form from the IRS website - they sometimes make small changes to the layout that could cause issues if you use an old version. The 2024 forms should be available now for reporting 2024 payments. Your plan gives you the best of both worlds: meeting the contractor deadline while traveling, and letting your CPA handle the official IRS submission properly when you're back. Don't let the pushback make you second-guess a solid approach!

Has anyone dealt with a situation where the ex-spouse refuses to share information about improvements they made to the property? My ex won't tell me what she did to the house after I moved out, but I know she finished the basement.

One thing to keep in mind is that since you haven't lived in the house for over 5 years, you'll be subject to capital gains tax on your portion of the profit. However, make sure you're calculating your basis correctly - it should include not just half of the original purchase price ($121,000), but also any qualifying improvements made while you owned the property. The fact that your ex was responsible for ongoing costs per the divorce decree doesn't change your tax basis, but any capital improvements made during your joint ownership period could increase your basis and reduce your taxable gain. Given the numbers you provided, you're looking at roughly a $31,000 capital gain ($152,000 - $121,000), which will be taxed as a long-term capital gain since you owned the property for more than a year. When entering this in TurboTax, make sure to indicate that you received a 1099-S and report your 50% ownership share. The software should walk you through the process, but double-check that you're only reporting your portion of both the proceeds and the basis.

Slightly off topic but why are u paying $12.99 per trade in 2025? Almost all major brokers offer free stock trades now. Unless ur trading something unusual or international?

Just wanted to add a point that might help others - make sure to keep detailed records of ALL your brokerage fees throughout the year, not just relying on your 1099-B. I learned this the hard way when my broker's year-end statement was missing some fees from smaller trades. I now keep a simple spreadsheet tracking each transaction with the actual purchase/sale price and the fee separately. This way when tax time comes, I can verify that my cost basis calculations are correct regardless of what the brokerage reports. Also, if you're doing a lot of trading like the OP mentioned, consider whether you might qualify as a trader for tax purposes rather than an investor - the rules for deducting expenses can be different and potentially more favorable.

Has anyone actually gotten penalized for not paying FUTA as a solo S-corp? I've been operating for 3 years and honestly haven't been paying it because my accountant told me it wasn't necessary. Now im kinda worried...

I went through this exact situation when I started my S-Corp two years ago. You definitely need to pay FUTA tax even as the sole owner-employee - there's no exemption at the federal level like some states have for unemployment taxes. Here's what I learned: You'll file Form 940 annually and pay FUTA on the first $7,000 of your wages. Even though your state exempts you from state unemployment taxes, you should still qualify for the 5.4% credit in most cases, bringing your effective FUTA rate down to 0.6% instead of the full 6%. The key is making sure you're categorizing your state exemption correctly on Form 940. I'd recommend double-checking with a tax professional or calling the IRS directly to confirm your specific situation, but don't skip filing - the penalties for not filing Form 940 can add up quickly.

Varo is usually good. Mine came early. Check your account details. Make sure they're correct. IRS doesn't make mistakes often. But it happens. Give it until end of day tomorrow. Then worry. Most people get their money on time.

I'm in the exact same boat! DDD 3/18 with Varo and still nothing as of this morning. Last year my refund hit 2 days early around 6 AM, so I was expecting it yesterday or today. I've been checking the app obsessively too! 😅 From what I've read, Varo's early deposit timing can be inconsistent - sometimes it depends on when the IRS sends the ACH files to the banks. I'm trying not to panic yet since we still have until tomorrow, but the waiting is definitely nerve-wracking when you're counting on that money!