I once had a job making $35,000 a year. 35K is a ton of money, but when you live in NYC it's only a moderately large amount of money. My employer was running what looked from my angle like a tax scam because they wouldn't give us ANY tax documents (W2, 1080-MISC, anything). I try to explain this to people and they don't understand at all. My employer had a complicated reason why this was completely legal.
After 5 years of complaints (no one knew which box to put "$35,000" into in turbo tax), they rounded up all 100 employees and brought their tax lawyer in to help us. It was the most bizarre meeting I've ever been in. For some reason, the tax lawyer was unable or unwilling to give us any tax advice. All we wanted to know was which box to put $35000 into each year when we do taxes. Half of us had been audited because our taxes looked fucked.
The tax lawyer gave a high level overview of taxes and benefits and laws and never would explicitely address our situation. If anyone asked a question about our specific situation he would say "that's a question you'll have to ask your tax professional".
Then a near riot broke out. The tax lawyer was going on vaguely about "taxable benefits" and started talking about the special circumstances when health insurance was a taxable benefit. It was just meant to be a stock slide about taxes. Collectively, everyone in the audience realized that his slide was telling us that our special employement status meant our health insurance was a taxable benefit. And no one had been paying taxes on this benefit for the last five years.
So there's one hundred people in a room that make poverty line money, just realizing they owe tens of thousands of dollars in back taxes, and every time they try to get an honest answer out of a millionaire, they're told to talk to a tax professional who would surely charge $200 an hour. It got really ugly fast.