Just be careful about the timing of all this. I closed my LLC last year but made a mistake in the sequence and it cost me. Make sure you: 1) File your final tax return first 2) THEN dissolve with the state 3) THEN cancel any local licenses/permits 4) THEN notify vendors, banks, etc. If you dissolve with the state first, you might have trouble filing your final tax return because technically the business no longer exists. I learned this the hard way and had to reinstate my LLC temporarily just to file properly.

Great advice in this thread! I went through a similar situation last year with both an LLC and sole proprietorship that had been mostly inactive. One thing I'd add is to make sure you handle any outstanding business debts or contracts before filing for dissolution. I almost forgot about a small monthly software subscription I had for the LLC and a couple of vendor accounts that were still open. Even though the amounts were tiny, having open obligations can complicate the dissolution process. Also, if you have any business bank accounts, don't close them until after you've filed all your final returns and received any potential refunds. I made the mistake of closing my business checking account too early and had to deal with getting an IRS refund sent to a closed account - took months to sort out. For the sole proprietorship side, since you mentioned selling on eBay/Amazon, make sure to update your tax settings on those platforms so they stop sending 1099s to that business name/SSN combo. Otherwise you might get confusing tax documents next year.

The community college near me offers free tax preparation through their accounting program! Students get real-world experience and you get free tax help - even with self-employment income! I'm SO ANGRY that the IRS and tax prep companies don't advertise these options more widely!!! Check your local community colleges, universities with accounting programs, or even law schools. Many have IRS-certified volunteer programs that can handle self-employment returns at no cost. You deserve access to free filing regardless of your income source!

I wish I had seen this thread earlier this tax season! As someone who just started freelance consulting work, I fell into the exact same trap - spent three weekends trying different "free" platforms only to hit paywall after paywall once I mentioned my 1099-NEC income. What's really frustrating is that the IRS's own Free File page makes it sound like there are plenty of options, but when you actually try to use them, it's a different story entirely. I ended up using Cash App Taxes based on a recommendation from another forum, and honestly, it worked better than I expected. The interface was clean, it walked me through all the Schedule C stuff without trying to upsell me, and both my federal and state returns were actually free. My only advice is to gather ALL your business receipts and expense documentation before you start - having everything organized made the process so much smoother. Thanks for sharing your experience - it's reassuring to know others have navigated this successfully!

Has anyone mentioned the mortgage interest deduction limits? If you're filing separately, the limit for mortgage interest deduction drops from $750k to $375k of mortgage debt per person. If you have a larger mortgage in a high-cost area, this could be significant.

Great discussion everyone! As someone who's been through this exact scenario, I want to add one more consideration that saved us a lot of money: the Net Investment Income Tax (NIIT). At your income level ($410k), you're definitely subject to the 3.8% NIIT on investment income if filing jointly (kicks in at $250k for joint filers). But if you file separately, the threshold drops to $200k per person, which might actually work in your favor depending on how your investment income is distributed between you and your husband. If most of your investment income is in one spouse's name and that spouse makes significantly less than $200k, filing separately could help you avoid or reduce the NIIT. This is especially relevant if you have rental properties, dividends, or capital gains. Also, don't forget about the Additional Medicare Tax (0.9%) which has similar thresholds - $250k joint vs $200k separate. The interaction between these taxes and your local tax situation could be the deciding factor. I'd definitely recommend running the numbers with all these factors included, not just the basic income tax calculation. The savings from avoiding these additional taxes might outweigh the loss of other joint filing benefits.

Something worth noting about the CAF number format - if it helps with your confusion between 8 and B, the IRS typically uses character positions strategically. Having a mix of numbers and letters in the same field would make database management more complex, which is why the standard is 8 numbers followed by 1 letter. The letter at the end is often used as a control character or identifier for internal IRS purposes.

Good practice to double-check! You're absolutely right to be cautious about the CAF number format. As others have confirmed, it's definitely 8 numeric digits followed by 1 alphabetic character, so your instinct about position 8 being a number (not a letter) is correct. One tip that might help in the future - when you receive your CAF number notification from the IRS, you can also verify it by logging into your IRS e-services account if you have one set up. Your CAF number will be displayed there in digital format, which eliminates any handwriting interpretation issues. This is especially helpful for tax professionals who need to reference their CAF number frequently throughout filing season.

One important thing to remember: even if you select "Partnership" on Venmo because that's your only option, make sure all your OTHER documentation and filings are consistent with being a single-member LLC. For example, if you're banking, insurance, state filings, etc. - always identify as a single-member LLC. The Venmo classification is just for their internal purposes and doesn't change your actual business structure. I made this mistake last year and it created confusion with my bank when they saw different entity types on different documents.

For what it's worth, I called Venmo business support about this exact issue for my single-member LLC. They told me to select "Partnership" when using an EIN for a single-member LLC. The representative explained that their system requires one of those three categories when using an EIN, and Partnership is the closest match for a single-member LLC. Apparently it's a common question they get.