Has anyone actually gotten audited because of late 1099s? I'm in a similar boat but I'm worried filing them now will trigger some kind of review.

I went through this exact situation last year with 3 late 1099-NECs and can share what worked for me. First, don't let your accountant's casual attitude stop you from doing the right thing - filing late is always better than not filing at all. I was terrified about penalties too (facing $840 total), but I filed them electronically through the IRS FIRE system and included a detailed reasonable cause letter. The key points I emphasized were: 1) This was my first offense with a clean compliance history, 2) The contractors had already reported the income on their returns, 3) I was voluntarily correcting the issue without IRS contact, and 4) I had legitimate confusion about the filing requirements. The IRS approved my first-time penalty abatement request and waived all penalties. The whole process took about 6 weeks from filing to getting confirmation. No audit, no additional scrutiny - just relief that it was handled properly. My advice: file them ASAP electronically, write a sincere letter explaining your situation, and don't let fear of an audit stop you from complying. The IRS actually appreciates voluntary compliance more than you'd think.

Has anyone just asked their tax preparer about this? When my wife and I file jointly, our accountant actually includes a breakdown of how much each of us contributed to the total tax liability and what portion of the refund "belongs" to each of us.

This is such a relatable situation! My partner and I went through the same thing our first year filing jointly. We ended up using the withholding proportion method that Fatima mentioned - it felt the most fair since it directly reflects what each person "overpaid" during the year. One thing that helped us was also considering our different tax situations beyond just income. For example, I had more pre-tax deductions through my employer (401k, health insurance), which reduced my taxable income but also meant my withholding rate looked lower. We factored that into our discussion. For this year, I'd suggest going with the withholding-based split since it's straightforward and fair. But definitely consider setting up a system for next year - whether it's a joint tax account like Connor suggested or just agreeing on a method upfront so you're not debating it every April!

I'm surprised nobody has mentioned Form 8308 yet. When there's a sale or exchange of a partnership interest, the partnership has a filing requirement to report the transaction to the IRS using Form 8308 (Report of a Sale or Exchange of Certain Partnership Interests). This is required if there are Section 751 assets involved. Make sure the partnership's tax preparer is aware of this transaction so they can handle this reporting requirement correctly. I've seen partnerships miss this form, which can create problems later.

This is a really comprehensive discussion! I'm dealing with a similar situation right now and wanted to add one more consideration that might be relevant. If your client has been receiving guaranteed payments from the LLC (like for management services), make sure to clarify whether any portion of the sale proceeds might be attributable to those future guaranteed payments. Sometimes in these partner buyouts, part of the purchase price is actually compensation for giving up future guaranteed payments rather than just the equity interest itself. Any portion that's really compensation for guaranteed payments would be ordinary income, not capital gain. It's another layer to analyze beyond just the Section 751 hot assets. The partnership agreement and sale documentation should help clarify this, but it's worth discussing with your client to make sure the economic substance matches how the transaction is structured on paper. Also, if the selling partner has any outstanding loans to/from the partnership, those need to be factored into the overall transaction analysis too.

Don't sleep on free filing options through the IRS Free File program if your income is under $73,000. I used OLT (Online Taxes) through this program last year and it was completely free for both federal and state, with a surprisingly good interface.

I've been using TaxSlayer for the past three years and can't recommend it enough! Started using it when I was in a similar situation with multiple income sources (W-2 from my main job, 1099s from consulting work, and some investment income). What I love about TaxSlayer is that it doesn't constantly try to upsell you like TurboTax does - you pick your plan upfront and that's it. The interface is clean and intuitive, and it walks you through everything step by step without feeling overwhelming. For your situation with 2 W-2s and a 1099, their Simply Free version might even work, but their Classic plan (around $25) handles everything smoothly. The customer support is also surprisingly good - I had a question about reporting some freelance expenses last year and got a helpful response within a few hours via chat. Much better experience than the big names for way less money.

has anyone actually received a 1095-a BEFORE filing their taxes? i swear they always come late and then the irs gets mad when you file without it. such a broken system lol.

I've been through this exact scenario! The key thing to understand is that the IRS computer systems often have "sticky" flags from previous years. Since you had marketplace coverage in 2023, their system is still expecting 1095-A documentation even though you correctly switched to employer coverage. Here's what worked for me: First, call the IRS practitioner priority line if you can get through (or use one of those callback services others mentioned). Explain that you switched from marketplace to employer coverage and only have a 1095-C for 2024. They can often remove the flag immediately. Also, when you file your amended return, include a statement explaining the insurance change. Write something like "Taxpayer had employer-provided health insurance for all of 2024 as evidenced by Form 1095-C. No marketplace coverage in 2024." Attach it to your 1040-X. The $2,800 refund will come through once this gets sorted - just takes patience with their system!