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've heard you can deduct mileage for driving to job sites, but what if the work was at multiple houses in the same neighborhood? Do I track each trip separately or can I just estimate the total miles for all the jobs?

You need to track each trip separately for proper documentation. Keep a mileage log (there are free apps for this) showing the date, starting location, ending location, miles driven, and purpose of each trip. For multiple houses in the same neighborhood, each location is a separate job site. So if you drive from home to House A, then to House B, then back home, you'd record three legs: home to A, A to B, and B to home. The total mileage is deductible as long as each trip has a business purpose. Many people miss out on this valuable deduction because they don't keep good records, but it can really add up!

Your brother is giving you terrible advice that could get you in trouble. ALL income legally needs to be reported. The IRS has gotten much better at finding unreported income through bank deposit analysis and other means.

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).

Thank you for this insight! I hadn't considered the "local parent" angle. I'm definitely providing a large chunk of support (probably around 60% when you factor in housing, insurance, and day-to-day expenses), but we've always had her claim him since she's the biological mom. Do you know if there would be any downsides to changing this arrangement? Would she lose out on any tax benefits if she didn't claim him? We file separately since we're not married.

The main consideration would be comparing the total tax benefits each of you receive by claiming the child. For your girlfriend, not claiming the child could mean losing the Child Tax Credit (currently up to $2,000 per qualifying child), potential Head of Household filing status (if this is her only dependent), and possibly the Earned Income Credit if her income qualifies. For you, claiming the child would allow you to use your HSA for the child's medical expenses, potentially claim the Child Tax Credit yourself, and possibly file as Head of Household rather than Single. I'd recommend calculating both scenarios - one where she claims the child as usual, and another where you claim the child - to see which provides the better overall benefit for your household combined. Sometimes it makes sense to alternate years if the math works out better that way.

This is actually a really smart workaround. HSA rules focus on who pays the qualified medical expense, not where the money originally came from. If the person claiming the dependent is the one making the actual payment to the healthcare provider, it should comply with the rules.

Thanks for the clear explanation! I'll let my brother know that for next year they should coordinate better. It was such a hassle last year with the paper filing. Do you know roughly how long the amended return takes to process before the mom could file? Just wondering about timeline since tax deadline is coming up.

The IRS is currently taking about 16-20 weeks to process amended returns. It's a much longer timeline than regular returns, unfortunately. Your brother's situation highlights why it's so important to coordinate within families. Given that the filing deadline is approaching, the parent might want to file an extension using Form 4868 to give extra time for the child's amended return to be processed. This extends the filing deadline (not the payment deadline if taxes are owed) for six months. The extension would give plenty of time for the amendment to be processed before the parent needs to file their complete return. Just remember that if the parent expects to owe taxes, they still need to pay the estimated amount by the original deadline even with an extension.

I used TurboTax last year to fix a similar dependent issue with my son. When you're in the "Personal" section, there's a question specifically asking "Can someone claim you as a dependent?" Make sure that's set correctly. For amending, you need to go to "Tax Tools" then select "Amend a return" option. It walks you through the changes step by step. The confusing part is that TurboTax sometimes phrases questions differently depending on which version you're using. The free version has less guidance than the paid versions. If you're stuck on a specific screen, I can try to help!

Thanks for the help! I found the section you mentioned. It was buried in a submenu I kept missing. The wording was definitely confusing - it asked something like "Did anyone provide more than half your support" which wasn't immediately obvious was about dependency. Their interface definitely needs work!