Well, there's the rub. You can do all the background work you want but there are no guarantees of playing time once the season starts.
If your player is getting playing time now, likes his team, likes his living situation, likes his coaches and the coaches are good coaches that run good practices, then he should stay with that team unless he gets an opportunity at a higher level. Coach is more likely to rely on him more and more as a veteran player and he should get more opportunities next season. Probably better than starting over on another team and having to prove yourself all over and earn a role on that new team.
I knew a kid that was in the USHL last year, younger kid, back end of the bench, not happy about the lack of playing time but happy to be playing Tier 1 juniors. Just kind of hanging on. This year rolls around and as a veteran returner thinking there will be an increased role this season. Nope, cut out of training camp. Is playing in the NAHL now and having a good season. Should have been playing in the NAHL last season instead of watching from the USHL bench, no clue how much that year of lack of PT hurt this kid's development. I'd like to think that if Covid wasn't around last season they would have sent him down but that situation last year resulted in a lack of player movement as teams tried to isolate themselves.
Point is there are no guarantees, and, players need to play in order to develop.