I think Doc may go 10-11 deep this year. I usually don't approve of doing that, since I think that the best players should play the maximum amount of minutes they can without hurting their health or production. However, given the age of some on this team, the need to work in new players, and the potential to drive up trade value on some players, I'd be OK with it for the regular season.
I do, however, think Wilcox's status as a rotation member may be in question if he doesn't get healthy soon. Darko, Sullinger, and Bass have all looked strong. Factor Green (and obviously KG) into the PF mix, and there really isn't room for anyone else, especially someone who hasn't shown he deserves minutes (even if it isn't his fault).
As for trade value, I think to some extent that's the idea. However, let's keep in mind that our depth also negates one of the reasons you make a trade: for depth. Thus, if we make a trade, it's going to have to be for a star caliber player. There's no point in trading two bench players for two bench players, particularly when we have depth at every position.
And I'm not sure Danny will necessarily be able to drive up the trade value of what we have on our roster to quite make that work by this trade deadline. However, I do think that's a long term goal for him either for next summer or next year's deadline.