My brother and I did it part-time in the late 80's. The only weapon I ever carried was an axe handle (And I never used it). A previous poster (R H Lee) hit the nail on the head:
Good repo men use stealth and deception, not intimidation and threat of lethal force.
I'm not sure how it works everywhere but when we were doing it, repossessing cars was far less glamourous/dangerous than it is in the movies.
For example, we'd get a list of cars and addresses from the finance company. They would also give us the keys to the cars. That's right, we had the keys. I never broke a window or popped an ignition in the two years that I did it.
The first thing we'd do was go to the person's house and knock on the door. By then, the repossessee had received several letters, so it's not like we were giving up the element of surprise. We'd show them the paperwork, explain that we were just doing our job, remind them that they were going to lose the car anyway, and ask if we could please have the car. This would work 8 out of 10 times. If not, we had to find a way to take it.
It was great when we could get the person's work address - you'd always find the car during the day, in the open (they were often boxed in by other cars when the person was home - after all they knew the car was going to be repossessed). It's too bad that few of these people worked for a living.
It was more difficult to get a car that was at someone's house. Dogs were a problem. You were often working at night and people are more likely to have a gun in the house than on their person. Think about it, I'm sneaking around their yard in the middle of the night - they have no idea whether I'm there to rob them or what. We tried to aviod having to do this. In addition, cars were often parked in driveways with other cars behind them. Once, my brother got in a boxed-in car and drove it around the back of the house (through the yard). If either of us got a bad feeling about any situation, we'd just leave and come back another time.
The only time we had a problem was when we had a car that we'd been trying to get for about two weeks. We took a ride by the house just as someone was leaving with the car. We followed for a couple of blocks and the person stopped at a convenience store. The guy ran in and left the car running! I hopped in and drove away with my brother in the chase car. We got about 4 miles and got pulled over by a cop with his gun drawn. The guy had reported the car stolen! It took a few phone calls and a couple of hours and we got it squared away.