Hasta La Motion!

Hey, need help creating the clone effect for a particular shot:
the person will be cloned in car. same person driving, same person in the passenger seat and two more (same person) in the back seats (window seats). decided to shoot at night to avoid any discontinuity from shadows during the day. i’ll be lighting the subject in each seat with a car lighting rig so lighting wont be an issue I’m shooting on a canon 7d and will probably edit the sequence in fcp7. not sure if fcp7 can do what i’m looking to do but i’m sure after effects will.

question 1: how should i go about shooting this to successfully clone my subject without making it look amateur?

question 2: which program for masking would you recommend?

question 3: i hate that i ruled out shooting during the day because the shot would’ve been a lot better. any suggestions for shooting during the day?

thanks a lot