1. Never heard of having to wire taxes as a condition of receiving stock owed to you. Your taxes are between you and the IRS. Sell-to-cover should be considered standard if the stock is liquid. Any reputable company working with any reputable broker should be able to manage it.
2. Lawyer
3. Ridiculous. Lawyer
4. So they can do sell-to-cover, they just don't want to for some reason.
If the equity amounts to a significant amount of money, you would probably benefit from consulting your own attorney. Don't take advice on an internet forum and definitely don't accept "Trust Me Bro" from the company. Good luck.
Low sample count for me, so I guess I'm lucky I've never seen this. My first thought would be the same as OP's: This smells funny. Generally whenever you have to pay your employer to get paid, something foul is afoot.
2. Lawyer
3. Ridiculous. Lawyer
4. So they can do sell-to-cover, they just don't want to for some reason.
If the equity amounts to a significant amount of money, you would probably benefit from consulting your own attorney. Don't take advice on an internet forum and definitely don't accept "Trust Me Bro" from the company. Good luck.