Assuming Caldwell is better than Starks and Wilson, which by all accounts is obvious, here is what the rotation should be.
PG: Caldwell, Starks, Wilson (spot time when someone is struggling)
SG: Gilder, Starks
SF: Hogg, Flagg
PF: Williams, Trocha
C: Davis, Trocha, Jasey (spot time when someone is in foul trouble)
I redshirt Chandler if he's ok with it and I can trust Hogg to stay available throughout the season.
PG: Caldwell, Starks, Wilson (spot time when someone is struggling)
SG: Gilder, Starks
SF: Hogg, Flagg
PF: Williams, Trocha
C: Davis, Trocha, Jasey (spot time when someone is in foul trouble)
I redshirt Chandler if he's ok with it and I can trust Hogg to stay available throughout the season.