It rarely is on the terms of the player when you're talking about clubs of our size. They might want to stay here for life but also few want to end it as bit-part players, which is what Del Piero increasingly was. Much in the same way Raúl was for Real Madrid by the time he left.
My thoughts on Del Piero are the same now as then - the time was right even if he didn't agree with it, and might even have been a season too late. When you're scrapping for a start against Matri, Vucinic and Quagliarella it should show a few pointers.