In theory, I like the idea because I think Orlando is definitely more likely to end up in the toilet than we are.
What I would do however is eliminate Houston from the conversation. I am not big on Asik and I've heard Houston wants two 1st rd picks for him. See ya.
I would just strictly deal with Orlando.
Maybe something like this (and not sure it works money-wise)
Celts get Afflalo, Glen Davis and Jason Maxielle.
Orlando gets Bradley, Crawford, Olynyk, the 2014 Brooklyn/Atlanta pick and Humphries.
For Orlando, we take another bad contract of their hands in Baby plus I like Maxielle. You could also play either one at center. They also get expiring contracts, another draft pick and basically get really bad
For Celts, we get a legit scorer, two more big guys who can help us make a playoff run. Besides, dealing that 2014 Brooklyn pick (to me) isn't a big loss because it looks like that pick is going to be Atlanta's and Atlanta isn't that bad of a team right now.