How much did it end up costing to fix the mistakes? I'm trying to weigh the cost of hiring a pro versus doing it myself.

The direct cost to fix the mistakes wasn't huge - about $350 for a tax professional to prepare and file the amended returns. However, the real cost was the time and stress. It took almost 6 months to get everything sorted out with the IRS, including several follow-up letters and clarifications. The bigger issue was that I had to explain to family members why we received unexpected IRS notices, which was uncomfortable and made me look incompetent. Looking back, I would have gladly paid the $800-1200 that a professional would have charged originally to avoid all that hassle. Trust taxation has some unique rules that most DIY software doesn't explain well, even if it technically supports the forms.

Huge difference! A revocable living trust typically doesn't require a separate tax return at all - the income is usually just reported on the grantor's personal return (Schedule E). The trust you're describing is likely what's called a "grantor trust" for tax purposes. What OP is describing sounds like irrevocable trusts that are separate taxpaying entities requiring Form 1041 returns. Those are much more complex.

But isn't it still worth claiming even if it's small? I always thought you should take every credit you qualify for, no matter how small. Plus doesn't it help establish a pattern of claiming it for future years?

Yes, it's technically worth claiming because every dollar counts. Even if it's just $5-29 back, that's still money you're entitled to. And you're absolutely right that it helps establish the habit of claiming the credit in future years when your contributions will hopefully be larger. I didn't mean to suggest skipping it entirely - just providing perspective on the time/value tradeoff. If you're using tax software, it should handle Form 8880 pretty easily, making it definitely worth the few minutes to enter your contribution. My main point was to focus on increasing those retirement contributions going forward, as that's where the real value is long-term.

This is a really important point! I actually qualified for the Savers Credit last year but didn't get anything from it because I already had zero tax liability after my other deductions and credits. Spent all that time filling out Form 8880 for nothing.

Do they have good support if you get stuck on something? I'm worried about messing something up and getting audited.

Their support is decent but not as comprehensive as TurboTax's. They have email support that usually responds within a day and a good knowledge base with articles explaining most common tax situations. The audit risk is pretty minimal if you're just reporting things accurately. The software does have accuracy checks built in that will flag anything that looks unusual or might trigger an audit. I was nervous my first year too, but it really walks you through everything step by step. If your tax situation is fairly straightforward (W-2 income, mortgage, charitable donations), you should be fine. The peace of mind might be worth paying a bit more for TurboTax if you're really worried, but I found FreeTaxUSA perfectly adequate.

You can definitely still find an accountant this time of year, but many good ones are already at full capacity. I'd start calling around asap. My sister just switched in February and found someone, but she had to call 8 different places before finding one accepting new clients.

What if your contract says you're a contractor but the company treats you more like an employee (making you work specific hours, etc)? Does the contract override how they actually treat you?

The contract doesn't override reality. The IRS looks at the actual working relationship, not just what the paperwork says. This is called the "economic reality test." If a company is controlling when, where, and how you work, requiring you to work certain hours, closely supervising you, providing equipment, and treating you like an employee in practice, the IRS will consider you an employee regardless of what your contract says. Many companies try to save money by misclassifying employees as contractors, but the actual working relationship is what matters.

I filed SS-8 last year. Takes FOREVER (like 6-8 months) to get a determination, but when I finally did, the company had to reclassify me and pay all the back employment taxes. They weren't happy lol but it solved the problem permanently.

The Donor Advised Fund sounds interesting! If I bunch several years of donations together, would that help me stay under the IRMAA threshold for multiple years, or just give me one good year and then potentially push me over in subsequent years? Also, do you know if medical premiums count toward that 7.5% threshold? I have some pretty hefty supplemental insurance costs.

Bunching donations can give you one year with a lower MAGI, which helps with IRMAA for just that determining year. You're right that you'd need to plan for the subsequent years too - that's where QCDs become helpful since they can reduce your taxable income each year without needing to itemize. Yes, your premiums for Medicare Part B, Part D, Medicare Advantage, and supplemental policies all count toward the 7.5% medical expense threshold! Many retirees don't realize this. Track all your out-of-pocket medical costs including dental, vision, hearing aids, and long-term care insurance premiums too. With the higher healthcare costs in retirement, you might be surprised how often you can clear that 7.5% threshold.

That's really interesting! How much did you have to invest to make it worthwhile from a tax perspective? I've been thinking about helping my son with his landscaping business but wasn't sure if it would make a meaningful impact on my taxes.