A couple of thoughts about putting DiPietro on waivers:
A while back, and in another sport, the San Francisco 49ers signed their quarterbacks to long term contracts, both partially to lock them in, and also to backload the contract. This meant that San Francisco was going to pay out more money as Montana and/or Young came to the end of their contracts, even if they wren't playing. This ended up burning the San Francisco franchise over a number of seasons. You'd think that other franchise owners would have paid attention and said "nope, don't want to do that". The DiPietro long-term contract has had the extra added flavor of DiPietro seeming to spend more time on the IR than in the net.
It's a harsh thing to say, but having a player on an ultra-long term contract who spends a lot of time injured, and who doesn't end his career by injury is the worst possible outcome for the franchise.
Given that the Islanders just acquired Tim Thomas's contra...