a long time ago. And this fantastic human-being wants to re-apply with a new email, etc. Is it a waste of time or should he go for it?
Ask him to go for it and tell us what happened next. That way, he's experience will prove fruitful and we will know if its a waste of time or not.
I'm not an expert, but Google wants to make money, so they're not going to be that hardcore with their screening process. I say go for it.
The only reason would be that he/she is violating Google's TOS. Were there promoting something that violate's Google's terms of service?