I don't like packing.
When I look around my house, I see the progress I've made towards living a less-stuff lifestyle, such as advocated by Paul Graham, among many others, (see Stuff.) Still, I don't think I'll reach the point where I can comfortably live out of a suitcase or a backpack without significantly reducing the quality of my life.
So what about a service more like AirBnB + PODS + A Closet organizer something like this + Robotic movers similar to these = Easy, comfortable, continuous travel.
Just playing with numbers on the back of an envelope, I think this would be both possible and cheap, in the near future.