As someone mentioned around the AS break when it was unclear will we trade Ray, ABs ceiling is Tony Allen with better IQ and offense, Ray Allens ceiling is... Ray Allen.
Problem I see with Ray resigning is that eventhough everything falls our way ( Danny gets some pieces, KG decides we can contend and comes back) he will have that phone call from Doc telling him he is going to Memphis fresh in his head. I think similar to KG, eventhough he is extremely loyal, Ray wants to play last few years for a contender, and wont risk puting him self in situation where he could end up in washington or bobcats if Danny thinks he can get an Mayo type upgrade for him (bit worse player, but younger).
To avoid that Danny would have to give him no trade clause in his contract which I highly doubt.