If I could ask a CPA anything, I'd want to know about tax planning strategies that actually work for middle class people. Not the fancy stuff for millionaires, but practical ways regular people with W2 jobs and maybe a side gig can legally reduce their tax burden. Like, are FSAs and HSAs worth it? Should I be making traditional or Roth contributions? Is a 529 plan actually good or are there better ways to save for my kid's college? When is it worth itemizing vs taking the standard deduction?

I'd ask a CPA about all these tax prep software options. Is TurboTax really worth the money? Are there better alternatives? And what things should I absolutely NOT try to DIY even with software help? I always worry I'm missing something major by doing my own taxes.

One thing to consider that hasn't been mentioned - while there's no AMT implication when exercising underwater ISOs, there could be benefits to this strategy beyond just starting your holding period clock. If your company does a new 409A valuation in the future and the price goes up, exercising at today's lower strike price could save you money compared to waiting. You're essentially locking in your purchase price now, betting on future growth. Also, some companies have exercise windows when you leave - exercising gradually while employed can reduce the cash needed at separation. And depending on your company's stage, early exercise might have qualified small business stock (QSBS) implications that could potentially exclude large amounts of gain from taxes later.

A word of caution from someone who's been through this: just because you CAN exercise underwater options without AMT doesn't mean you SHOULD. I did this at my previous startup believing in their future - paid about $45k to exercise options below strike price. The company never recovered and eventually shut down. That money was completely lost. No tax deduction, no nothing. It's considered a capital loss when you sell or when the shares become worthless, but capital losses are limited to $3k per year against ordinary income (unlimited against capital gains). So while the AMT advice here is correct, make sure you're making this decision with eyes wide open about the company's actual prospects, not just hope. Exercise only what you can afford to lose entirely.

Another possibility - could this be related to an ex-spouse or business partner? I had a similar situation where my ex-husband's accountant kept making estimated tax payments under my SSN for a business I was no longer part of after our divorce. Took years to untangle because nobody at the IRS could figure out where the payments were coming from. Make sure you check with any past business associates or family members who might have your SSN on file for some legitimate reason. Sometimes these mysteries have simple explanations.

dont cash those refund checks!!! my cousin did something similar and got hit with penalties later when they fixed the system error. the irs will eventually figure it out and want all that money back with interest. just keep all the letters they send you and maybe talk to a CPA not just the regular irs people on the phone. sometimes the irs computer systems dont talk to each other and the right hand doesn't know what the left is doing.

Just to add from someone who used to work at the IRS - the CP30A is one of the "good" notices. It means they've zeroed out a tax assessment, often due to an appeal, amended return, or correction. If your online account shows zero balance, you're completely fine. Don't waste your emergency leave on this. The IRS actually issues these notices so you have documentation that a previously assessed amount has been canceled, which is protection for you.

If you're getting USPS Informed Delivery, can you also set up mail forwarding to someone you trust? My brother is deployed and I receive all his important mail and scan it for him. Might be worth setting that up for the future so you don't have these situations where you can only see partial documents.

You might also be dealing with a misclassification issue. Some small construction companies incorrectly treat employees as independent contractors. Did you get paystubs with tax withholdings or just straight cash payments? If they didn't withhold taxes, they might be trying to issue some weird hybrid form that doesn't make sense.

Make sure you file on time even if this isn't resolved! You can file Form 4852 as a substitute W-2 based on your best records of what you earned. If you have paystubs, bank deposits, or even a written record of hours worked × your hourly rate, use that to calculate your income. Then file an amended return later if needed when you get the correct W-2. Don't let their mistake cause you to miss the filing deadline!