It Takes a Thief (2005)

Think your home is well protected? Ex-burglars Matt Johnston and Jon Douglas Rainey will prove you otherwise.
Matt and Jon look for homes which would be targeted by thieves. When they find one, Jon goes off elsewhere while Matt tries to convince the homeowner to allow Jon to try to break in. If they say yes, Matt goes through the house and shows them their security flaws and learns a bit about how they approach security. Then, cameras are installed in every room of the house and the homeowners get a chance to completely lock up their house. They wait in the van and watch on TV as Jon breaks into their house and steals anything and everything he likes. After he leaves (usually in the homeowner's automobile), Matt takes them in to to see the damage. Jon returns to the "scene of the crime" and meets the homeowners. They review everything that was stolen and the cleaning crew puts it all back while a security watches over the