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Just a data point - I did exactly this last year for my 2022 taxes. Contributed the max to my HSA in March 2023 (for tax year 2022) and immediately withdrew it to cover medical expenses I'd already paid out of pocket. Worked perfectly and saved me about $900 in taxes. My tax software (TurboTax) handled it well, but make sure you get Form 5498-SA from your HSA provider showing the contribution was designated for 2023, and keep your medical receipts organized. I created a simple spreadsheet tracking each expense, date, amount, and payment method that I keep with digital copies of all receipts.
Did you have to get any special form from your doctors or hospitals for the expenses, or just your regular receipts? My hospital bills don't specifically say "qualified medical expense" on them.
Don't forget that you'll need to fill out Form 8889 with your tax return to report both the contribution and distribution. It's pretty straightforward but the instructions can be confusing. Line 2 is where you'll put your $3,850 contribution for 2023. Line 14a is where you'll report the distribution amount. Line 15 is where you'll report that the entire distribution was used for qualified medical expenses. Your HSA provider will send you Form 5498-SA showing your contributions and Form 1099-SA showing your distributions. Make sure the contribution is coded properly as a 2023 contribution.
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Something nobody's mentioned yet - if you're really concerned about this from a legal perspective, you might want to consider forming an LLC. It's pretty simple and inexpensive in most states. That would make the distinction clearer since you'd be an LLC rather than a sole proprietor, but you could still be an independent contractor in terms of your relationship with clients. For tax purposes, a single-member LLC is typically treated as a "disregarded entity" and you'd still file Schedule C unless you elect different tax treatment.
That's an interesting suggestion! Would forming an LLC change anything about how I file taxes or would I still use Schedule C? And would there be any benefits for someone making such a small amount ($3k-ish per year) from this work?
You would still use Schedule C with a single-member LLC unless you elect to be taxed as an S-Corporation or C-Corporation. The LLC doesn't change your tax filing method by default - it's considered a "disregarded entity" for tax purposes when it has just one member. For someone making only around $3,000 annually from this work, an LLC probably isn't worth the administrative costs and annual fees unless you have significant liability concerns. The main benefit of an LLC is limiting your personal liability, but for patient advocacy work with minimal income, the protection may not justify the expenses. Some states have annual LLC fees of $800+ (California), while others are much cheaper ($50-100).
Has anyone used TurboTax for this kind of situation? Does it automatically put you on the right forms? I'm starting to do some freelance work this year and trying to figure out if I should use software or hire someone.
I use TurboTax Self-Employed and it works great for this. It asks if you have self-employment income and then automatically puts you on Schedule C. It doesn't really distinguish between "independent contractor" and "sole proprietor" either - it just asks about your business income and expenses. The software walks you through all the deductions you might qualify for too.
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Here's another factor I haven't seen mentioned yet - timing matters with these decisions. If you take the refund as cash, you get the money now. If you invest that money for a year before you need to make your next state tax payment, you could earn additional returns that offset any tax difference. Just another angle to consider in your decision.
But don't you have to pay quarterly estimated taxes if you're anticipating a tax bill? So you couldn't really wait a full year to make that payment, right?
You're right that you might need to make quarterly estimated payments - it depends on your total expected tax liability and other withholdings. If you have sufficient withholding from other sources (W-2 job, etc.), you might not need to make estimated payments. Even with quarterly payments though, you still have the benefit of having the money available to you for some period of time versus having it immediately applied to next year's taxes. You could potentially use it for higher priority needs before making those estimated payments when they're actually due.
One other thing to consider - some states give interest on refunds if you take them as cash rather than applying forward. My state gave me 3% interest on my refund last year because of processing delays. That's another reason taking the cash might be better than applying forward!
I don't think most states pay interest unless they're really late with the refund processing though. Did you have to wait an unusually long time?
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Former tax preparer here. One thing to consider is that if your parents have been going to the same person for years, that preparer might actually know important details about their financial history that could be relevant. When I had regular clients, I would often remember things like "oh, didn't you sell that property back in 2019? We should check the basis calculation" that they might forget. That said, $500 is definitely on the high end for a simple return. Maybe go with them to their appointment this year and see what the preparer actually does? You might get a better sense of whether they're getting value or being upsold on unnecessary services.
Is there anything specific to watch for to know if they're getting their money's worth? What kinds of questions should I ask the preparer?
Watch for how much time they spend asking questions about your parents' situation - good preparers should be inquiring about life changes, medical expenses, charitable donations, and changes in income sources. They should explain why they're making certain choices on the return. Ask what specific deductions or credits they're applying that might be missed with self-filing. Also ask if there are any tax planning suggestions for next year - good preparers offer this. If they're just entering W-2s and a few 1099s without much discussion, your parents are probably overpaying.
I'm gonna be the devil's advocate here - just let your parents do what makes them comfortable. My mom insisted on paying $350 to Liberty Tax every year even though I showed her how simple her return was. I finally gave up and realized that for her, it wasn't about the money but about the comfort and routine. For that generation, taxes are scary, and the peace of mind is worth the cost. Maybe offer to split the difference - like suggest a cheaper tax service but don't push the completely free DIY option if they're resistant.
This! I tried forcing my dad to file online and he made a mistake that cost way more than what he would have paid a professional. Sometimes it's not worth the battle.
Xan Dae
Just to add some extra info: even if your 1099-C has errors or is missing some elements, you still need to report it. If you don't and the IRS gets a copy (which they will), you'll get a notice asking about the discrepancy. Better to report it and attach an explanation if needed. I went through this last year when my student loan servicer sent a 1099-C with the wrong box checked. I reported it as issued, then included a statement explaining the error. Saved me from getting one of those scary IRS letters months later.
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Fiona Gallagher
•If I get a 1099-C for a debt that was actually paid, not canceled, what's the process for disputing it? Do I still report it?
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Xan Dae
•Yes, you should still report it even if you plan to dispute it. The best approach is to include the 1099-C information on your return, then attach Form 8275 (Disclosure Statement) explaining why you believe the debt wasn't actually cancelled. The key is to immediately contact the issuer in writing requesting a corrected form. Keep detailed documentation of all communications. If they agree it was an error, they should issue a corrected 1099-C showing zero cancellation amount. Once you receive that, you can file an amended return if needed. This approach shows good faith compliance while you're resolving the dispute.
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Thais Soares
FYI banks don't always get these right. My credit union sent out 1099-Cs to everyone who closed accounts last year by mistake lmao. They had to send out a mass email saying to ignore them. If ur bank sent a bunch out "accidentally" maybe check if they made a system error?
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Nalani Liu
•Wow, that's wild! Did they send corrected forms or just tell people to ignore them? Seems like the IRS would still have the incorrect info.
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