1) No, it does not work on it.
2) The printer booster upgrade is unlimited uses so long as you have it on yourself at the time of dropping the printer. As for the PBH, if you're referring to a printer hacker then no it is not.
3) No I don't think so.
4) Handcannon's are pretty strong and cheap but if you don't know what you're doing you'll lose it pretty fast.
5) As far as I know the cars that can knock around other ones the most are the Lamborghini and Special Car.