P5:
Make friends in the campgrounds and you'll always have a helper. That said, there are numerous aids out there for hooking up trailers. There are cheap back up cameras, and even [urlhttp://garage-toys.com/alquichitgui.html]these things that mount to your trailer and hitch[/url] that help you line them up. Really, I hook up my boat ALL THE TIME without any help. And I do it backing up the driveway mouth which slopes into the street.
I really think the flippac is pimp. I'd like to get one for my truck one day.
Westies are fun, but not much for living in them unless you're a dirty old hippy. They make great weekend toys for flyfishing in the mountains.
Yes, the gas engine vans are that weak. The springs are not set up for towing in most of them. The engines are usually on the small side, small V8s like the 305, and with all the added weight of the "conversion", they are just not set up for it.
Another bene of going the truck route would be to go 4x4. I've seen conversion vans stuck in campground parking lots, on the beach, and on back roads before.....