Part of his job is to confront squatters in abandoned homes, who can strip a home of its value or ruin it completely. Colpaert showed "Nightline" a home where the hot water tank had been stolen. He said squatters find creative ways to enter homes.
"They'll send little kids in the smallest of basement windows first, stuff like that … they'll kick [the window] in and send a little kid in first to come and open the door for the rest of the way."
Colpaert said incentives often work better than force when it comes to getting people to comply, including a proven tactic called cash for keys. Colpaert offers the debtor money in exchange for a promise to keep the home in sellable condition before moving out.
"Everyone's happy," he said. "Well, I don't know how happy [the debtor] truly is, but he's got a nice check that'll help him maybe start a new life."
Colpaert admits that his job is starting to get frustrating. "Every mile I have to drive and every moment I have to spend on this silly account I could be doing something else. But that's what they pay me for. So that's why I do what I do."
For Henderson, every repo is a victory, but victory isn't always sweet.
Take the case of Martin Lautner, a victim of cutbacks in the auto industry whose beloved vessel Seas the Dream is his no more.
"Well, when I bought the boat in 2003, it was 10 percent of our income, and we don't have any kids, and I love the water, so it seemed like a good choice. Now it's 60 percent of our income, and it's the boat or the house," Lautner said.
There's an old expression that the two best days in a boat owner's life are the day you buy it, and the day you get rid of it, but that wasn't true for Lautner.
As Seas the Dream sailed away, he took one final look. For Henderson, it was also a time to reflect.
"I hate to see it happen to people like that," he said. "That guy could have been your father, that could have been my father."
The repo man, it turns out, does have a heart. Just don't ever count on seeing it.