Some questions:
Why George Lucas de Paula over Cotton. Seems like an uneccesary change only for the sake of making a change. COtton has earned it.
Why 10 deep when playoff rotations are not that deep? Usually 8-9 guys.
I see that Booker, Burks and Burke are MIA. You mention that you have no idea how this would happen. Did you look to see what range these players in the draft are going at? That might help you come up with some of your own ideas.
Why the desire to revamp our wings when you have Hayward, Hood, Burks and Millsap under contract? That is a nice collection. Who do you see as the weak link and why?
Yay, actual thoughts

Anywho
-De Paula- I see as an asset grab, I think he will turn out much better than what a late first/early second would cost us. If he doesn't it doesn't cost too much, if he does he's a potential asset in the future (think Schroder). But if we weren't willing to or unable to get him then cutting him from the plan for Cotton doesn't really have any great effect.
-10 deep mostly for injuries, and for the fact that lots of these guys are young, likely a few of them wouldn't turn out how I'd hoped. RHJ/Booker/Jaiteh being guys I'd see losing minutes in a playoff scenario.
-Burks is the big one on what would happen to him, not really sure. Tried to express that we had a lot of options with Booker- part of a trade to take back salary and get picks, keep him(probably no Holmes in that idea-duplicate each others offense though I feel Holmes will be the superior defender), maybe as a piece, lots of options. I use Draftexpress as my usual guide for prospect value- Booker(15), RHJ(22), De Paula(28), Jaiteh(35), Holmes(50). I see De Paula and Holmes fluctuate a bit from other sources so I averaged them to around late first/early second. Burke I see as late first round value at this point, maybe just a straight up flip by having somebody pick Jiateh/De Paula and then trading with them.
-I like all of our wings individually but I don't really love them as a collective. Hayward is obviously the best of the lot so I feel he's the one we should look to build around. One of Hood/Burks is great but I feel like having both of them is a little redundant, I'd like to flip one of them for a 3/D player(Booker is the player I see filling that best in the draft) to play with the starting lineup and have the other come off the bench to lead that squad. I like Millsap but I have my doubts, basically hoping to replace him with a bigger/younger version of the same role with RHJ.
And really the big key of it all is Teodosic, if we don't think we could get him then adding all this additional youth without a fairly knowledgeable vet and keeping Exum as the starting PG probably would work out really terribly.