Re: Brandon Roy
I'd take him for 20-25 minutes a night. Limit him throughout the whole season so that he's fresher for the playoffs. Limit his minutes to important minutes in the 4th quarter or in close games. Have him be RIP's backup. Have him be the secondary ball handler.
Limit his minutes for the majority of the season, but then later in the season if or when Rose returns gradually increase his playing time a bit to build that chemistry with Derrick.
Basketball wise it would definitely work, just hope that he's relatively healthy and can handle the load of an NBA season even if it means playing half the minutes he was used to he could still be very valuable.