I think this is an interesting idea. A couple of things I'd mention, commentary not criticism.
Waiters:
Waiters is such a weird asset right now. I get the feeling everyone knows he's a talented player, but the last 2 seasons all of his crazy has been publicized enough that it's a trade off now. You get a young SG with obvious NBA talent...but you also very likely get JR Smith 2.0. What GM subjects his young team to that kind of mess? I don't want him on the C's and his personality is 100% the reason. Even the Bucks need to step back and measure that. They're essentially trading the potential of Henson for Waiters and expirings. I wouldn't make that deal unless a 1st round pick was involved. Even then I think twice.
Milwaukee:
A Sanders for Waiters swap doesn't seem terribly one-sided for the Bucks. If I have to have a knucklehead I guess I want him to be 7ft tall. Losing both Sanders and Henson for basically Waiters and expirings is a really bad trade for them. Even with a mid-1st rounder it's probably a bad deal for them.
Boston:
Would be a ok trade for us. Not sure it's a home run. First, we probably wouldn't want to pay Thompson with Sully on his rookie deal for at least 2 more seasons but Henson for KO is a good swap for us at this point. Henson is lanky but he'll continue to put on weight. He's still fairly young (23) so there is definitely still time for him. We might offer up a 1st to swap KO and Henson but it would have to be the Clippers which is #15 or #16 right now. I wouldn't trade KO+2015LAC for Hanson right now. Henson hasn't shown much growth since he was drafted and 1st round picks are just too valuable now, especially with contracts going up.
Cleveland:
They pass on this. Sanders is a huge knucklehead and it's tough to see this as an upgrade considering they lose Thompson and Waiters. Thompson to KO is a downgrade and Waiters for Sanders might make up that ground but there is no guarantee. They would be making this trade trying fix cohesion problems. That can be really treacherous.
Overall I think that Milwaukee gives up too much and Boston gets too much. If the Bucks get the 2015 LAC pick from us it makes some sense for them. As a Celtic fan I don't really want Waiters or Thompson, for roster fit reasons. Additionally I just don't want Waiters attitude. Dude is too sketchy to throw in a young locker room right now, at least in my opinion.
I think if I saw this thread on a random sports forum I'd be able to tell it was a Celtic fan posting
Not that it's a bad idea, but it tilts toward us pretty significantly. If we give up the LAC pick it gets closer but it's not good enough for the other two teams.