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.

How far back should you keep student account statements? I'm worried I might be missing some documentation if I need to go back and check my 2021 stuff.

I'd recommend keeping all student account statements for at least 3-4 years, which aligns with the general IRS record-keeping recommendations for tax documents. This gives you enough time to address any issues that might come up with education credits or if you're audited. For accessing past statements, most schools keep these records accessible in your student portal for several years after graduation. If you can't find them online, contact your school's bursar office - they can usually provide account histories going back many years.

Yes! The IRS actually says you should claim based on when you paid, not necessarily what's on the 1098-T. I had to override my tax software warnings last year because my December payment for Spring semester wasn't reflected properly. Just make sure you have documentation (bank statements, receipts, etc.) showing when you actually made the payments.

I hadn't considered quarterly payments. Do you just divide your estimated annual interest tax by 4 and pay that amount each quarter? Are there specific deadlines I would need to remember? I'm worried I might forget and then end up with penalties anyway.

Yes, you can divide your estimated annual interest tax by 4 for equal payments. The deadlines are April 15, June 15, September 15, and January 15 of the following year. I just set calendar reminders. You don't necessarily have to make equal payments though - you can adjust each quarterly payment based on how much interest you've actually earned that quarter. This is especially helpful if your interest income is unpredictable. The IRS Form 1040-ES has worksheets to help you calculate this. The key is making sure you've paid enough throughout the year to avoid the underpayment penalty.

Not everyone can just move their money into tax-advantaged accounts though. What if you need access to your savings before retirement? Roth has penalties for early withdrawal and I-bonds have to be held for at least a year. Some of us need more liquidity than that provides.

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).