Just wanted to add that even though the 1095-C codes can be confusing, it's still important to keep the form for your records. While the IRS does receive this information directly from employers, having your own copy helps if there are any discrepancies later. For your specific situation with codes 1E and 2F, those indicate you were offered qualifying coverage that met ACA requirements. But as others have mentioned, you'll want to verify you actually enrolled by checking your pay stubs for premium deductions or contacting your insurance carrier. One thing I learned the hard way - if you had coverage through your employer for the full year, you generally don't need to do anything special on your tax return regarding health insurance. The individual mandate penalty was eliminated for 2019 and beyond, so there's no penalty for not having coverage. The main time you'd need to actively report health insurance info is if you're claiming premium tax credits for marketplace coverage, which wouldn't apply to employer-sponsored plans.

That's exactly right, Miguel! Since the individual mandate penalty was eliminated starting in 2019, you don't need to actively prove your health insurance coverage on your tax return just to avoid a penalty. The 1095-C is primarily for IRS record-keeping and to show that your employer offered qualifying coverage. With codes 1E and 2F, it sounds like you were offered comprehensive, affordable coverage through your employer. As long as you actually enrolled (which you can verify through pay stub deductions or by contacting your insurance provider), you had qualifying health coverage for the year. The only time you'd really need to get into the weeds with health insurance reporting on your tax return is if you purchased coverage through a marketplace and received advance premium tax credits, or if you're claiming other specific health-related tax credits. For standard employer-sponsored coverage, you can generally just keep the 1095-C for your records and file your taxes normally. It's understandable that all these codes are confusing - the health insurance reporting requirements were much more complex when there was still a penalty for not having coverage. Now it's mostly just administrative record-keeping between employers and the IRS.

Quick question - does anyone know if tax software like TurboTax handles this kind of cash income reporting well? Or is it better to use a specialized self-employment tool?

Just wanted to share my experience since I was in almost the exact same situation last year! I was doing landscaping and pet sitting for neighbors, all cash payments, and made about $3,800. You definitely need to report it all on Schedule C - there's no minimum threshold for reporting income, even if it's just $50. What really helped me was setting up a simple notebook where I wrote down every payment as soon as I got it. Date, amount, what the work was for. Super basic but it saved me when tax time came. One thing that caught me off guard was the self-employment tax. Since you made over $400, you'll owe about 15.3% of your net earnings for Social Security and Medicare on top of regular income tax. It's calculated on Schedule SE. But remember you can deduct business expenses - gas for driving to jobs, tools you bought specifically for the work, even supplies for dog sitting like leashes or treats if you provided them. The whole thing seemed overwhelming at first but once I got through it the first time, it wasn't nearly as bad as I expected. Just keep good records and you'll be fine!

Let me add a wrinkle most people don't know - if you distributed any business assets to yourself during the dissolution (like computers, furniture, etc.), that needs to be reported as a liquidating distribution on your final 1120-S. The corporation is treated as having sold these assets to you at fair market value. I completely messed this up when closing my S-corp and ended up having to amend returns. Cost me an extra $400 in accounting fees!

I went through this exact same situation with my S-corp dissolution last year and want to emphasize something that might save you some headaches - make sure you also cancel your EIN with the IRS after everything is filed and processed. Even after filing all the final returns (1120-S, Form 966, etc.) and getting state dissolution completed, I kept getting IRS notices asking about missing tax returns for subsequent years because the EIN was still active in their system. You have to specifically write to the IRS requesting EIN cancellation and include copies of your dissolution documents. Also, if you had any business bank accounts, credit cards, or merchant services tied to your EIN, close those ASAP. Some banks will report 1099s to closed business EINs which can trigger more IRS correspondence down the road. The penalty situation sucks, but as others mentioned, first-time penalty abatement is usually granted if you've been compliant in the past. Get everything filed immediately to stop the bleeding, then deal with penalty relief afterward.

Just wondering - have you looked into equity compensation restructuring? If a portion of that $1.1M is from stock options, RSUs or other equity comp, there are timing strategies that can make a huge difference. I saved nearly 6 figures last year by working with my employer to adjust my vesting schedule and exercise timing.

Given your income level, I'd strongly recommend looking into conservation easements if you own any land or are considering real estate investments. These can provide substantial tax deductions - sometimes 4-5x your investment - while preserving land for conservation purposes. Also, consider a defined benefit pension plan if you have any self-employment income or consulting work on the side. These allow much higher contributions than traditional 401ks - potentially $200k+ annually depending on your age and income. One strategy that's often overlooked is bunching deductions into alternate years. Since you're likely itemizing anyway, consider prepaying property taxes, state taxes (up to the SALT cap), and charitable donations in alternating years to maximize the benefit. Finally, if you're married, look into spousal IRA contributions and income-splitting strategies through family partnerships for any investment income. The key at your level is having multiple strategies working together rather than relying on any single approach.

Has anyone tried bunching charitable deductions? With the higher standard deduction ($29,200 for married filing jointly in 2024), we've started doing this where we donate 2-3 years worth of charitable contributions in a single year so we can itemize that year, then take the standard deduction in the off years. We're also looking into donor-advised funds where you can get the tax deduction immediately but distribute the actual charitable gifts over time. Anyone have experience with these strategies?

One strategy you might be overlooking is a backdoor Roth IRA conversion. Since your MAGI is over $146K and you can't deduct traditional IRA contributions, you could still contribute $7,000 to a non-deductible traditional IRA, then immediately convert it to a Roth IRA. This won't reduce your current tax liability, but it's tax-free growth for retirement. Also, since you mentioned having kids, make sure you're getting the full Child Tax Credit ($2,000 per child under 17). The credit phases out at higher incomes but doesn't start until $400K for married filing jointly. Another option: If your employer offers a cafeteria plan or flexible spending account beyond just healthcare, you might be able to redirect some compensation to pre-tax benefits like commuter benefits, life insurance premiums, or dependent care assistance. Finally, consider timing any major purchases or medical expenses. If you're close to the 7.5% AGI threshold for medical deductions, you might bunch medical expenses into one year to exceed the threshold.