Thinking back to when I was a boy---.
I've always lived in the Western 'Burbs of Chicago. My Dad came from the Southern area of Georgia, where his people mostly remained. Every year we would go down to see the Grandparents, aunts, uncles and so on. Two days driving down Rte 41.
That makes for a long ride, and it gets boring pretty quick. Especially through Indiana, and truth to tell Georgia can get a bit tedious when you're seven years old and you're just watching it out the car window. Now I try to imagine being cooped up in a truck for weeks at a time--- this might not be the best plan you ever had. It's fun at first, but--- trust me on this--- it'll get old rather quickly, especially if you're on a tight delivery and you don't have time to do anything fun. Or you're at a delivery where children aren't allowed (a surprising number) and the kids have to stay in a room while you finish the job. I can think of a lot of reasons why this doesn't work well.
I can see taking the kids on a trip of a couple of days, especially in a situation like mine where I drop the load then come back clean (you can do some sightseeing on the way back) but any longer than that I'd really want to think three times before I try something like that.