IF KG and Pierce retire/are moved, then yes I'd roll the dice. Amare can be an excellent (borderline unstoppable) 1 on 1 player when healthy. I think his lack of production recently has been due to being in a Melo-centric offensive system that is not suited to him at all rather than his decline of skill/health.
His contract is only 2 more years longer and we wouldn't do much in those 2 years without Pierce and KG anyways. It'd be fun to see what Rondo and Amare could do together.
If we could get a future 1st out of it, then I'm even more inclined to do so.
If Pierce and KG come back, then I would not do this under any circumstance, no matter how many picks come back to us. I think Amare would be an OK fit here (not great but better than NYK), but not worth the risk of losing those 3 role players. I think those 3 guys are much better than people on cb give them credit for.