"Well, we are on a travel team, and are enjoying getting alot of good experience, but we are winning very few games."
I can take this question/statement in a different direction. Winning is very dependent on level of competition. There are teams that have very good records, but when you look at who they are playing you quickly figure out why. Then there are teams with sub 500 records that come in and shut you out. At 14u he needs to "enjoy getting alot of good experience".
"Should I look to get him on a different team"
Tough to answer without direct knowledge of situation, but I would start by asking if the current organization has a track record of getting guys to the next level. Be cautious about moving teams and do your homework. The grass isn't always greener.
"Secondly, one reason he was placed on this team is that he can catch, even though its not his best position. He enjoys it, but i just doubt, that Catching is where his future lies."
Don't automatically discount this move by the coaching staff. Especially if the coach has been around the block a few times, and your kid shows interest in the position. This can turn into a lot of future leverage for your kid. Everyone is always looking for a solid catcher. The great ones are not that common, and have an extremely large impact on that winning percentage you touch on previously.
Also, this statement makes me believe that the travel org has different teams (A-B-etc..) at the same age. If so then you need to ask yourself a few more questions. Off the top of my head: What events does the A team play, how competitive are they, and more importantly do they put the top kids from their organization on this team?