15 Has anyone used TurboTax Self-Employed for this kind of situation with both W-2 and freelance income under an EIN? I'm trying to figure out if I need to pay for that version or if the regular Deluxe would handle it.

Just want to add that you're making the right choice keeping your EIN! I had the same situation - regular W-2 job plus freelance consulting with an EIN. The filing process really is straightforward once you understand it. One tip that saved me time: when you're filling out Schedule C, make sure you select the right business code for your consulting work. The IRS has specific codes for different types of consulting (management, computer, etc.) and using the correct one helps avoid any follow-up questions. Also, since you're married filing jointly, your spouse doesn't need to worry about the EIN at all - it's just your business identifier that appears on the Schedule C portion of your joint return. The income will flow through to your main 1040 and get combined with your other household income for tax calculation purposes.

Anyone else notice how the IRS says your 1120-S was "two months late" when it was actually one month and a few days? They count partial months as full months for penalty calculations. So even if you're just ONE DAY late into a new month, they charge you for that entire month. Totally frustrating but that's how they calculate it.

I just went through this exact same situation last month! Filed my 1120-S on April 15th thinking I was on time, then got slapped with a $480 penalty notice. The March 15th deadline for S-Corps really catches people off guard. I called the IRS and asked specifically for "First-Time Penalty Abatement" (as others mentioned, you HAVE to use those exact words). The agent reviewed my filing history, confirmed I'd been compliant for the past 3 years, and approved the abatement on the spot. No forms to fill out, no documentation needed beyond my EIN and the penalty notice number. The whole call took about 25 minutes including hold time, and I got the confirmation letter 2 weeks later showing $0 balance. Definitely worth making the call before just paying it - the IRS is surprisingly reasonable about genuine first-time mistakes when you have a clean compliance history.

It might be helpful to know that what you're experiencing isn't technically an "audit" in IRS terminology. It's likely what they call a "compliance review" or "documentation request" which happens during initial processing. True audits generally occur after a return is fully processed, often months or even years later. These pre-refund reviews are actually somewhat less concerning, as they're usually focused on specific items rather than your entire tax history. If I were in your position, I would probably just provide the requested documentation promptly and clearly labeled. These reviews are fairly routine, especially for returns with home office deductions, and typically resolve quickly when you provide organized documentation.

I went through this exact situation two years ago with my Schedule C business expenses. My transcript showed absolutely nothing, but I got a letter requesting documentation for my vehicle deductions and office supplies. It was so confusing at first! What I learned is that the IRS has automated systems that flag certain returns during the initial intake process - before they even hit the main processing queue. They call it "pre-refund verification" and it's actually more common than you'd think, especially for returns with business deductions, home office claims, or certain tax credits. The good news is that these pre-processing reviews are usually much faster and less invasive than actual audits. I organized all my receipts, mileage logs, and supporting documents into clearly labeled folders with a cover letter explaining each category. Sent it in within two weeks and my return was processed normally about a month later. Pro tip: Keep digital copies of everything you send them. The IRS has been known to "lose" documentation, and having backups saved me when they asked for the same info again six months later due to a clerical error on their end.

From my experience as a startup employee with ISOs, here's the real deal: companies often try to keep the 409A valuation (FMV) as low as possible while still being defensible to the IRS. This helps employees avoid immediate tax hits. The VC valuation is almost always higher because they're buying preferred shares with liquidation preferences and other rights. Your company should have documentation about the most recent 409A valuation they had done. Ask specifically for that. For AMT purposes, that's the number that matters - not the VC round price. If the 409A valuation truly equals your strike price, you'd have zero spread and no AMT impact when exercising, which would be ideal.

Has anyone here actually calculated what happens to your AMT if you exercise a bunch of ISOs? I'm in a similar situation and trying to figure out if I should exercise now or wait.

Has anyone used a payroll service like Care.com or HomePay for this? I'm overwhelmed with the idea of figuring out the taxes myself even with guidance.

Great question! I went through this exact situation with my elderly father's caregivers last year. The IRS is actually pretty clear on this - if you're controlling when they work, how they do their job, and providing the tools/supplies, they're household employees, not independent contractors. The $2,600 threshold mentioned earlier is key - if you pay any household worker more than that in a year, you need to handle Social Security and Medicare taxes. At $24/hour for 20 hours/week, you'd hit that threshold in just over 5 weeks. One thing that really helped me was keeping detailed records from the start - work schedules, payment amounts, and job duties. The IRS looks at the totality of the working relationship, not just what the worker prefers to be called. Even if your caregivers say they'll "handle their own taxes," that doesn't change your legal obligations as the employer. I'd strongly recommend getting this sorted out sooner rather than later. The penalties for misclassification can be significant, and it's much easier to set up proper payroll from the beginning than to fix it retroactively.