The Rangers aren't going to trade Hank unless he asks to be moved. Gorton and JD dont want a Leetch situation possibly tarnishing their legacy. Hank asking for a deal is the better situation for the Rangers. They'd get to set the terms and tell Hank that he might need to be flexible with his destinations for contenting teams. Calgary isn't a desirable destination for Hank, but it might be one of the few teams interested in his services.
Do I think that request gets made this summer? No, but it could come at the deadline if the team is terrible and Hank is losing more starts to Georgie and Igor. The Rangers won't get a lot in a trade even at 50% retention. The deal will be about a final favor to a Rangers legend and turning the page on his tenure here. The Ray Bourque path.
I disagree with you on the timing.After meeting with JD and getting no extension and goal sharing duties it will force Hank to make the choice between being a mentor or move on for the Cup. Probably makes sense to have that meeting soon.