Travel can (and should) be a HUGE step up. He probably will sit for awhile until he gets accustomed to the better competition and the "play to win" versus "play for fun" attitude. The coaching is usually far better at the travel level and he should learn a great deal more.
One caution with travel hockey is the distances and the times that the games are held. (I think you are used to that though. Best friends are/were travel players and they have game start times of 9:00PM!!! Eff that.
My kids all started rec league and had to sit at the beginning when we moved up to travel. It was good for them. They didn't get on the soccer field until their understanding of the team concept matched their individual skills (which also improved with the better coaching).
ETA - The cost for all the latest hockey gear will make your investment in your daughter's swimsuit look like pocket change.
