Every kid is different, some kids need to be on a winning team in order to enjoy the game, others don't. Do whatever is best for your kid to keep them wanting to go to the rink. However, everything changes when the get older, you cant hold their hand forever and that's why most quit or loose the love. Good luck, its not an easy balance.
it is all about your kids development. Are the coaches and program skills, challenging him to become a better player? Maybe your team has one strong line and your playing teams that have 2-3? Is your goalie hurting your team giving up too many soft goals? There are plenty of reasons for losing and your record should not cloud your kids development.