A lady contacted me about joining my xcountry tour. It didn't state in the ad that it was to be self-contained, but that was in my very first e-mail, along with other essential points. About a week later, she wanted to have a van since it wouldn't cost too much for it or the driver (failing to mention that it would be her hubby driving their van). I nixed that very quickly because it would've changed the whole dynamics of the trip. If we'd taken her up on it, then you've got their relationship to worry about (is he going to get bored?), potential stealth camping would be difficult (how do you hide a van?), etc, etc.

It's probably a nice way to travel, but it really does depend on what you're trying to get out of the trip.