How much stock is Portland putting into Mike Bibby defensively? How willing is Portland to sit Bibby and put in Holiday or West in for high pressure situations? Holiday is a rookie, but one who is probably more defensively able, West is a bigger more athletic guy than Bibby, but is he tough enough to guard elite PG's?
Are you concerned about Rashard Lewis matching up against quicker craftier SF's? He's obviously a good offensive PF in the NBA, but as a SF if relegated to the perimeter, doesn't he lose a bit of his mismatch advantage? Its not like he's going to spend much time in the paint if JO and Shaq are in there.
Are you concerned with your depth at the SG/SF position? Redd Manu and Lewis are all very good players, but Fred Jones and Jared Dudley are not. Excepting Redd and Manu's injury histories, and age factor (ie each injury presumably takes a little bit out of them athletically, its just the aging process), Ryan Gomes and Fred Jones are going to see playing time..if not Fred Jones then Delonte, but then who plays your backup point behind Bibby?
It seems kind of like your perimeter rotation is like a tightly wound (is that the right word?) clock, and if one gasket breaks loose its just not going to run right. That's not to say its not a fine clock, but a vulnerable one. Injuries are a concern for every team, but with you double dipping between Lewis, Manu, and Delonte, do you worry that shortening your rotation one player screws the whole thing up?