Dungeon Siege question

A friend and I finally discovered Dungeon Siege multiplayer but one thing is confusing. OK, so I see that you can’t save your progress (seems really dumb), but we got to the first town and quit. I could start the next session in the first town, he had to start all the way back at the farmhouse. Any thoughts on why? What we did wrong? How I can jump him to the first town instead of making him walk all the way over by himself? Thanks.

IIRC, he either has to be of a certain level or he has to have visited the waypoint thingy (or I’m confusing DS with D2…).