Is it possible to file previous years' Form 8606 if you missed them? I've been making non-deductible contributions for 3 years but only learned about Form 8606 recently.

Yes, you can and absolutely should file Form 8606 for previous years if you missed them. You'll need to submit them separately as standalone forms - you don't need to amend your entire return. There's no penalty for filing Form 8606 late if you're only establishing basis (though there would be if you were reporting distributions). File a separate Form 8606 for each tax year, make sure to use the form version for that specific tax year, and write "Filed Pursuant to Section 301.9100-2" at the top to indicate you're filing it late under the automatic extension provisions.

Partial conversions are even trickier in TurboTax. Search for "1099-R" like others suggested, but when it asks what you did with the money, choose "Converted part to a Roth IRA." Then you'll need to specify how much went to the Roth vs how much stayed in the traditional IRA. The pro-rata rule will likely apply in your case since you kept some in the traditional IRA.

Good point about insurance! Also worth noting that some states charge higher registration fees for business vehicles vs personal ones. In my state, the business registration was about 25% higher. Something else to factor into the total cost equation.

That's super helpful! Did you need to provide any specific documents to the DMV to register it under your LLC? And did you run into any issues with insurance coverage when the vehicle was titled to your business instead of personally?

I had to bring my LLC formation documents and EIN letter from the IRS to the DMV. Some states also want to see your business license. The process was actually pretty straightforward - just took a little longer than a personal registration. Insurance was definitely different. My personal auto insurer wouldn't cover a business-titled vehicle, so I had to get a commercial auto policy. It was about 30% more expensive, but the good news is that commercial insurance is a legitimate business expense you can deduct. The insurance company wanted to know the percentage of business vs personal use, and they based some of their rates on that information. Make sure to shop around because the rates varied a lot between different insurance companies for the exact same coverage.

What kind of documentation did the engineering firm require? My concern is that since it's been a few years since purchase, I might not have all the original construction details or receipts they might need.

They actually needed less than I expected. They used the purchase documents, property tax records, and some photos I already had. They also did a virtual walkthrough where I showed them around the property using my phone. For components they couldn't see (like wiring, plumbing systems), they based estimates on industry standards for the building type and age. What really mattered was having a qualified firm that understood both the engineering aspects AND the tax rules. They documented their methodology carefully which is what protects you in case of an audit. The IRS doesn't usually challenge properly performed studies, even after-the-fact ones.

That's concerning. Was it a reputable firm that did your study? What specific documentation did the IRS say was lacking? I'm considering doing this too but worried about the audit risk.

It was short-term disability through my previous employer for about 6 months. I did receive some tax form from them but I'd have to dig it out. Does that make a difference compared to SSDI?

Yes, that makes a big difference! Short-term disability through an employer is handled very differently than government disability programs. If your employer paid the premiums for your disability insurance, then the benefits you received are likely fully taxable (you should have received a W-2 or 1099 showing this income). However, if YOU paid the premiums with after-tax dollars, then the benefits might be completely tax-free. If the premiums were paid with a mix of employer and employee funds, then a portion would be taxable. Definitely look for that form - it's crucial for determining how much, if any, of your disability payments are taxable. This directly affects your eligibility for various tax credits too.

This is a great point! I'm also a student parent and just found out I qualified for the American Opportunity Tax Credit which gave me $2,500 back even though my income was really low. Definitely worth checking if you're taking college courses.

How do you calculate the right amount for line 4(c)? Is there a formula or something? Also, is there any risk to withholding too much?

A quick way to estimate is to take the amount she owed this year ($320) and divide by the number of paychecks she receives annually. If she's paid biweekly, that's 26 paychecks, so about $12.50 per check. I suggested $25 to give a buffer for a small refund rather than owing. There's no real risk to withholding too much except that you're giving the government an interest-free loan of your money until you file your taxes and get a refund. Some people actually prefer larger refunds as a form of forced savings, even though financially it's not optimal.

This happened to me too! My employer reclassified me as a different type of employee with the same hours and slightly higher pay, but my withholding dropped by almost 40%. Ended up owing $900 and was NOT happy about it.