That's interesting - I hadn't heard about the Dependent Care FSA option. My dad is generally independent but has mobility issues that require some help. Would occasional home health aides or transportation assistance qualify, or does it need to be full-time care?

It doesn't have to be full-time care to qualify. If your father has legitimate mobility issues that require assistance, expenses for home health aides, adult day care, or transportation to and from care facilities while you're working would generally qualify. The key requirements are that the care must be necessary for your wellbeing (allowing you to work), and your father must live with you for more than half the year and be physically unable to fully care for himself. You'll need a doctor to document his condition and care needs. Keep in mind the $5,000 annual limit applies to all dependent care expenses combined, so if you have children also using this benefit, that's the total cap.

QPRTs are typically used for estate planning, not really for current tax benefits. It's where someone puts their house in a trust but retains the right to live there for a set period. After that period ends, the house goes to the beneficiaries (like children). The main benefit is reducing estate taxes by getting the house out of the estate at a discounted value. But it's complex and probably overkill unless your dad has a very valuable home and a large overall estate that might exceed the federal estate tax exemption (currently $13.61 million).

Thanks for explaining! That makes sense - my dad's house is only worth about $220k so probably not worth the complexity. I'll focus on the more immediate tax benefits mentioned above instead.

Thanks for bringing up the EITC! I actually don't have any dependents, it's just me. Would I still qualify? And would that be instead of the dental deduction or in addition to it?

You can still qualify for EITC without dependents, though the amount is smaller. For 2025, if you're single with no children and income around $24k, you might qualify for a small EITC (around $600-700 depending on your exact income). The EITC is completely separate from the dental deduction issue. You can claim both if you qualify for both. The EITC is a credit while the dental expense would be a deduction if you itemize. Credits directly reduce your tax bill dollar-for-dollar, while deductions just reduce your taxable income, so credits are generally more valuable.

Good point about the FSA, but it sounds like OP might not have benefits if they're making around $24k. Might be part-time or gig work. The FSA is only helpful if you have access to employer benefits.

Thats a really good point - I didnt even think about using a retirement account! Arent there penalties though if I need to take the money out before retirement age?

Yes, there are penalties if you withdraw the earnings before age 59½ - typically a 10% penalty plus taxes. However, you can always withdraw your original contributions (not the earnings) from a Roth IRA at any time without penalties or taxes. So in your example, you could always take out the original $20k anytime you want with no penalty. Only the $10k in gains would be subject to penalties for early withdrawal. This makes Roth IRAs more flexible than other retirement accounts while still giving you the tax advantages.

But be careful with wash sale rules! If you buy the same or "substantially identical" stock within 30 days before or after selling at a loss, you can't claim that loss for tax purposes. I learned this the hard way.

Wouldn't a bookkeeper be expensive for just a small tutoring income? Seems like overkill unless she's making significant money from it.

That's a good point about checking with coworkers. I'm friendly with a couple other people who started around the same time as me. I'll ask them to check their W-2s too. Do you know how I would go about filing a complaint with the Department of Labor if it turns out this happened to others too?

Most state Department of Labor websites have an online complaint form specifically for wage and hour violations, which would include improper withholding issues. Look for sections labeled "wage complaints" or "workplace rights" on your state DOL website. Before filing, gather all your documentation: your original W-4 showing you selected single with zero dependents, several pay stubs showing no federal withholding, your W-2 confirming zero withholding for the year, and any written communication with your employer about the issue. If coworkers had the same experience, ask if they'd be willing to be mentioned in your complaint.

Wait, so employers can just "accidentally" not withhold taxes and face zero consequences? That seems like a system ripe for abuse. Couldn't companies just "forget" to withhold as a way to effectively pay employees more without actually increasing their stated wages?