Wyse is an interesting case and I'll preface all I'm about to say with the admission that I have no idea what will happen and see him as a 50/50 flight risk. One that could go either way...
At the beginning of the season, I thought he needed to improve his skating, mobility and puck moving skills - but watching him, especially in the second half of the season, I think he has taken great strides (pun intended) in those areas. His combination of size, physicality and skill has to be intriguing to NHL scouts. I still think he has a fairly wide range of outcomes - there is a chance he's skating on an NHL third-pair in a few years, but it also wouldn't surprise me if he never really makes it past the ECHL.
It only takes one team to make an offer and if he gets a substantial bonus and a shot at the AHL, I think he probably should go. As you allude to, he's already 22 years old - so if he feels he is ready and a team is willing, the time to go is probably now. That said, there might be a handful of (or more) teams keeping an eye on him and hoping to see more development next season. Maybe he thinks (or will be advised) that further improvement will create a bidding war and better opportunities. I would look at a guy like Wyse (much more so than Gildon - who I really think has to move up) and wonder if maybe there is a real benefit to another year in college. If he can stay and handle a lot of pucks, instead of moving up and (potentially) being asked to play a physical/bank it off the wall type style, it might be better to do so...
I think two things might work in UNH's favor of keeping Wyse. First, he originally committed to Dartmouth and is a very strong student. Second, he has just one more year left (as opposed to two) and he might think he has a chance to do something special for UNH, aiding in a program-changing, turnaround. Agree or disagree from the outside looking in, I bet the players will feel that way at the end of the season. Three things working against UNH, assuming the opportunity arises, would be the dream of playing professional hockey, the significant financial opportunities and a team's vision for his future development...