Wait can you have a Solo 401k if you also have a 401k through your regular employer? I thought there were limits that applied across all accounts?

You absolutely can have both! There are two types of contribution limits: employee contributions (which are shared across all your 401k accounts) and employer contributions (which are separate). Since you're both the employee AND the employer for your self-employment business, you can still make "employer" contributions to your Solo 401k even if you've maxed out your employee contributions at your W2 job. The calculation gets a bit complex, but basically you can contribute around 20% of your net self-employment earnings as the "employer." This is completely separate from whatever your main job's 401k situation is. Many tax professionals don't even mention this strategy, but it's completely legitimate and can dramatically reduce your tax bill while building your retirement savings.

Your friend is playing with fire. You can only deduct the BUSINESS PERCENTAGE of vehicle expenses, and you need a detailed mileage log to prove it. The IRS specifically targets this area for audits. If he's claiming 100% business use for a personal vehicle, he's practically begging for an audit. And when they find out he's been using it personally too without documentation? Big penalties.

Does it matter which tax professional you use? Are H&R Block pros better than like a local CPA or the other way around?

It absolutely matters which tax professional you use, but it's not necessarily about brand names. H&R Block has some excellent preparers, but quality varies widely as it does with local CPAs. The key difference is typically expertise level and specialization. Most H&R Block preparers are trained in their specific tax preparation system and have varying levels of certification. A local CPA who specializes in tax might have more comprehensive knowledge, especially for complex situations like business ownership, investments, or unusual income sources. However, they often charge significantly more. The best approach is finding someone with specific experience in your particular tax situation, regardless of where they work.

FreeTaxUSA is WAY better and cheaper. I've used it for 5 years now with no issues. TurboTax deliberately hides free options and upsells you on stuff you don't need.

Thanks for mentioning this! I did have marketplace insurance in 2022 I think. Where exactly do I find those forms if I can't log into my old account?

If you can't access your marketplace account, you can call the marketplace directly at 1-800-318-2596 and request that they resend your 1095-A forms for the years you need. Make sure to have your personal information ready (SSN, DOB, address from that time). Alternatively, you might be able to get the information from the IRS by requesting a tax transcript, though sometimes these forms don't show up completely on the transcript. The best route is definitely going directly through the marketplace if possible.

How do you find someone who specializes in unfiled returns? Just search for "tax resolution" or is there some specific credential I should look for?

14 Could you explain more about this "step-up in basis" for inherited annuities? I thought that only applied to things like stocks and real estate, not annuities. Does it depend on when the original owner passed away?

20 The step-up in basis rules are complicated for annuities and depends on several factors. Generally, annuities don't receive the same full step-up in basis that other inherited assets might get. With annuities, what typically happens is that the income tax treatment passes to the beneficiary. So the taxable portion is still generally the difference between what was paid into the annuity (the cost basis) and its value at distribution. The step-up that can sometimes apply relates to the value at the date of death versus the original purchase price, but this varies based on how the annuity was structured and when the death occurred.

17 I tried that first actually! The customer service rep I spoke with just kept repeating that they "cannot provide tax advice" and directed me to consult a tax professional. Super frustrating experience.

Technically that would be tax fraud lol. But realistically you're right, nobody would ever notice or care about 6 cents. Still, I'd probably report it just to avoid any potential matching issues if the employer submitted it to the IRS.

Haha true about the tax fraud thing, but I wonder if there's actually a minimum threshold where the IRS just doesn't care. Like if you found a penny on the ground, you technically earned income but nobody reports that. I guess the difference is that this has an official W2 attached to it that's already in the system. You're right that reporting it is probably best just to keep everything matched up in their systems.

Box 14 is for "other" information that employers want to report but doesn't fit in the standard boxes. It could be union dues, health insurance premiums, educational assistance, or a bunch of other things. Usually not taxable, which might explain why Box 1 is empty - there were no taxable wages.