considering sully and oly shouldn't be players you build around and greg could, im not sure where you're going. but you also think highly of sully when no one else does.
Monroe might not be a position of need (though I wouldn't stop trading for him cause of Kelly and Sully) but he is probably the best asset you are going to get back from anyone. Boston has 0 leverage here, and probably wont even be able to deal him honestly.
Boston shouldn't be worried about fitting pieces into their team right now, they should just be getting the best players they can get. I say it all the time, you don't know where your team will be in two years, much less five years. Collecting the best players right now is the best bet, no matter if they fit or not. You will be better for it down the road.
If they dont make some major deal to bring in some more fire power this season, Rondo will leave in free agency. Best case scenario is letting rondo build his value and then trade him, but they better not let him go cheap.