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).

What about Credit Karma Tax? I heard that's completely free even for more complicated returns. Has anyone tried it?

Credit Karma Tax (now called Cash App Taxes) is completely free and handles most tax situations well. I've used it for returns with some investments and a side gig. The interface is clean and it covers most forms. The only downsides: it doesn't support multiple state returns, certain less common situations (like foreign income), and doesn't offer as much guidance as paid options. If your return is moderately complex but doesn't have those specific issues, it's an excellent free choice. Just be aware they make money by recommending financial products to you based on your tax info - that's the tradeoff for the free service.

Just want to add that if your income is below $60,000 you might qualify for free in-person help through VITA (Volunteer Income Tax Assistance). They're IRS-certified volunteers who will prepare your return for free. Google "VITA tax help near me" to find locations.

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.

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.