I think that violating a contract using a fake name is pretty risky. If you're going to do it on I2P-only services or something like that, maybe you'll get away with it, but the best way to avoid getting caught for a crime or contract violation is to not commit it in the first place.

I read sagas about people getting doxxed every day, even children. You may trust your opsec, but it only takes one slip-up to be out a large quantity of money. I wouldn't risk it.

What if you're already using your real name on stackoverflow? Then part of that money is to compensate changing names on various sites and perhaps losing history and it in general restricts things you can do for life.