I am significantly surprised that teams who find a good 4th or 3rd line player that they absolutely love haven't begun offering 'retirement' contracts to some of these guys. By this I mean:
Say the Rangers LOVE Acciari and have for a while. Other teams are offering 2 years x $1.5m. What is to stop Drury from offering 7 years @ $900k. Acciari gets a guaranteed $6.3m, of which, he may not be in the NHL for some of it based on his style of play but, at that point, the Rangers waive him therefore there is no penalty on the cap.
I said similarly for someone like Reaves last year. Drury should have given him a 3 year extension, not 1, but at $1m. If his play drops off, waive him. Then his cap hit is either gone or someone claims him.
Extending the cap hits out isn't a problem when they are below the minimum threshold that can be buried.
Of course the team would need to be cognizant of the 50 contract rule but let's be honest, that's not exactly hard. The Rangers have guys like Lindbom signed to NHL deals...