@AH82 - again, I'd suggest few things
1) first - lose the emotion - it is not going to get anywhere. You are whining and shortly no one is going to listen.
2) go back into the Turbo Tax program with your significant other and see how the check boxes work. You are arguing about your signficant other's choices and unless you understand how the program works yourself, you are not going to get anywhere talking to Turbo Tax
3) On the one hand you state that he didn't use live support:
They charged my boyfriend $200 for live self employed support. He is neither self employed nor did he use live services.
But then you go on the state
wouldn't a LIVE SUPPORT TAX EXPERT have stopped him and said "Sir, you are not self employed"?
so which is it? if he did not use Live Support, then no, a Live Support Tax Expert would not have stopped him from upgrading to self-employed
4) Please get your story straight. It is about to fall on deaf ears.
