That's good to know about the refund time limit. Do you know if filing for an extension would help with that deadline at all? And did you have to fill out any special forms to explain the guardianship situation to the Taxpayer Advocate?

Unfortunately, extensions only give you more time to file - they don't extend the three-year window for claiming refunds. That three-year clock starts on the original due date of the return regardless of extensions. For 2020 taxes (due in 2021), you're approaching that deadline, so prioritize that year first if possible. For the Taxpayer Advocate Service, you'll need to complete Form 911 (Request for Taxpayer Advocate Service Assistance), along with documentation of your guardianship/POA. Having your Form 2848 already completed helps. They're very familiar with guardianship situations and can sometimes help expedite transcript requests or provide guidance specific to your circumstances.

This is important. I made the mistake of not properly closing my dad's business when I became his guardian, and it caused all kinds of headaches years later. The state kept assessing annual fees and eventually sent it to collections because we thought just stopping operations was enough.

My employer actually picks the plan and pays the premium directly to the marketplace. They just give me this weird separate W-2 at the end of the year showing what they paid. So based on what you're saying, that would be the first scenario? And does that change how I should enter it in TurboTax?

Yes, if your employer selects and pays for the plan directly, that's more like traditional employer-provided coverage, just administered through the marketplace instead of a group plan. In this case, you would enter the W-2 normally in TurboTax, and the software should recognize that these amounts aren't subject to federal income tax. Just make sure when entering the W-2 that you include any codes shown in Box 12, as these codes tell the tax software how to treat different types of income. If your W-2 has code DD in Box 12, that explicitly marks the amount as employer-provided health coverage, which is not included in taxable income.

I've had issues with TurboTax too. Try checking if there's a code in Box 12 of your W-2 (like DD for employer health coverage). Sometimes TurboTax doesn't recognize these codes if you don't enter them exactly. Also worth reviewing the "Review" section before filing to make sure the taxable income calculation looks right.

Thanks for the tip! I'll definitely double check the Box 12 codes this time. I think last year I might have skipped over that part since I didn't know what those codes meant. Really appreciate the advice!

I actually asked about that last year, but my company said they can't do it because of how they control my schedule and work processes. Something about the IRS having specific tests for who qualifies as an independent contractor vs. employee. They also mentioned it would mean losing my benefits like health insurance and 401k matching.

That makes sense. The classification rules are pretty strict and the IRS looks at factors like behavioral control, financial control, and relationship factors. If the company controls when and how you work, provides tools/equipment, offers benefits, etc., they're probably correct that you should be classified as an employee. Be careful pushing for 1099 status just for tax deductions - if misclassified, it could create bigger headaches down the road for both you and the employer. The accountable plan route others suggested is probably your best option at this point.

This is what I did too. My company was resistant to dealing with expense reports, so they just increased my commission structure. Just make sure you do the math first - calculate what your annual mileage reimbursement would actually be (miles × IRS rate) and make sure the commission increase at least covers that amount.

1 That's a really good point I hadn't considered. If I amend 2021 to show the losses, would any unused losses potentially carry forward to the 2022 return? I'm trying to figure out the right sequence here.

3 Yes, exactly. Any disallowed passive losses from 2021 (amounts that exceed what you're allowed to deduct due to the income limitations) would carry forward to 2022. So first figure out your 2021 situation - how much loss you can actually claim after the Form 8582 calculations, then carry any remaining disallowed losses to 2022. Even if you can't deduct all the losses in either year due to the $150K phaseout, having them properly documented and carried forward is important because you can eventually claim them when you dispose of the property. That's why doing them in the right order matters.

10 I used TaxAct for a similar amendment last year. It was decent with Schedule E but the Form 8582 calculations were confusing. Had to basically understand the form myself to make sure it was done right. Not super user-friendly for rental property amendments.

What's this Mega Backdoor Roth thing? I've never heard of it and I'm maxing out my regular 401k already. Is this some kind of loophole?

The Mega Backdoor Roth is a completely legal strategy that allows you to contribute significantly more to Roth accounts than the standard limits. Here's how it works: after maxing out your regular 401(k) contribution ($23,000 for 2025), some employer plans allow additional after-tax contributions up to the total annual limit ($69,000 for 2025, minus employer contributions). You then immediately convert these after-tax contributions to Roth money either through an in-plan Roth conversion or by rolling them over to a Roth IRA. Not all 401(k) plans support this strategy though - you need a plan that allows both after-tax contributions (not just Roth) AND either in-plan Roth conversions or non-hardship in-service withdrawals. Worth checking with your HR department if your plan has these features. It's a game-changer if you're a high earner wanting to get more money into Roth accounts.

I did a spreadsheet calculation comparing both options. If your tax rate in retirement is exactly the same as your current rate, they're mathematically identical. But most people have lower income in retirement, which makes Traditional better in theory. But there's a strong case for Roth if: 1) You expect tax rates overall to increase in the future (likely given current deficit), 2) You expect to have other income in retirement keeping you in high brackets, or 3) You value the flexibility of Roth (no required minimum distributions, can withdraw contributions penalty-free if needed, etc).