FreeTaxUSA is good, but I switched to TaxSlayer because their self-employed package has better explanations of deductions specific to my industry. Also half the price of TurboTax.

Thanks for the TaxSlayer recommendation! I'll check them out next year. The industry-specific deduction guidance sounds really helpful. What I loved most about FreeTaxUSA was their audit assistance features and the clear explanations about self-employment tax calculations.

Thanks for bringing this up. My main job doesn't have any rules against outside work, but I should probably check if the second potential job would have an issue with it. And yeah, I'm a bit worried about burning out... do you think it would be manageable if I did the second job only 3-4 days a week instead of a full 5?

If you can get a second job that's only 3-4 days a week, that would definitely be more manageable than what I tried to do. I was doing 5 days at both places and it was crushing after a few months. Just be realistic about your energy levels and make sure you still have at least one day completely off to recover each week. And be prepared to adjust if you start feeling the effects. The medical bills from my burnout ended up costing more than the extra income I made from that period!

Not all jobs offer overtime though. I'm salaried and can work 60 hours and still just get my regular paycheck. It sucks.

Any recommendations on what income level typically makes it worth claiming? I'm in a similar situation with about $12k in AMT credits but not sure if my $110k salary will trigger enough regular tax to recover anything.

At $110k, you'll likely recover some of your credits, but it depends on your deductions, filing status, and other factors. If you're single with standard deduction, you'd probably begin to recover credits at that income level. Generally, I've found that married couples often need $150k+ combined income before recovering significant AMT credits, while singles can start seeing benefits around $90-100k. Consider consulting with a tax pro for a year-by-year projection based on your specific situation.

If you do a disqualifying disposition (selling before meeting holding requirements), it gets even more complex. The good news is you'll generally receive an AMT income adjustment that can help recover some of your AMT in the year of sale. The bad news is you'll pay ordinary income rates on the spread instead of capital gains rates.

That's great advice about the transcripts! I just requested them online. Do you know how long it usually takes to get them? And would filing a complaint against the accountant actually help my case with the IRS at all?

You should be able to access your transcripts immediately if you set up online access. If you requested them by mail, it typically takes 5-10 business days. The transcripts will show all reported income, your filed return details, and any payments or credits applied to your account. Filing a complaint against the accountant probably won't directly help with your current IRS issue. The IRS generally holds taxpayers responsible for their returns regardless of who prepared them. However, if there were truly egregious errors or misconduct, documenting it officially could potentially help if you need to request penalty abatement based on reasonable cause. It's also just good for consumer protection so others don't experience similar problems.

Yes! I disputed a CP2000 from 2016 just last year. The key is having documentation. In my case, I had records showing I'd already paid the amount through withholding that wasn't properly credited. If you can prove your case with solid documentation, the year doesn't matter as much as having the evidence.

That's really encouraging to hear! I've been stressing about this thinking I had no chance. Luckily I'm somewhat of a document hoarder and kept all my stock transaction records from my brokerage. Going to start putting together my response letter this weekend.

Wait, employers can match 529 contributions? I had no idea that was even a thing! Is that common? My HR department never mentioned anything like this when going over benefits. Do you work at a large company or something?

It's definitely not as common as 401k matching, but it's becoming more popular as an employee benefit, especially at larger companies and in industries competing for talent with families. About 11% of employers offer some form of 529 contribution or matching now. Ask your HR department specifically about education benefits - sometimes they don't promote it well or it might be buried in your benefits handbook. Even smaller companies sometimes offer this benefit. Mine started it last year as part of a "family-friendly" initiative. The company contribution is considered taxable income for federal purposes, but the tax credit/deduction on your personal contribution still applies.

Great question about Ugift! In most states, only the account owner (you) can claim the tax benefits for 529 contributions, regardless of who actually contributes the money. That means gifts from family members to your child's 529 through Ugift typically won't qualify for anyone's state tax deduction or credit. However, a few states (like Colorado and Virginia) have special provisions allowing non-account owners to claim deductions for their contributions. Your family members would need to check their own state's rules if they're hoping for tax benefits.