I hope Martell Webster will get some time a shooting guard this season, but I also take into account the situation they have in Portland. Webster will have to share time with incumbent Juan Dixon and the rookie Roy at shooting guard and Travis Outlaw and Darius Miles at small forward. I think Webster will eventually see thirty minutes a game but I don't know how long it will take for him to get there.
J.R. Smith will probably good for a over a three per game but talk about Carmelo playing time at shooting guard and going with a big lineup brings serious questions about how much playing time J.R. will really get. Kevin Martin>>>J.R. Smith.
As far as my pushing another point guard: I think you are set as far as rebounds and blocks go so I was recommending getting another guy who can shoot threes. I push point guards because a lot of them will get you a similiar amount of points, threes and steals as shooting guards, but as a bonus they also get assists. Although I don't know the makeup of the rest of your league, I would I be fairly confident in saying that you probably have rebounds and blocks wrapped up (unless someone has Kirilenko and Josh Smith on the same team). Since you will already be dominant in rebounds, blocks and most likely points, I thought you could improve your assist totals while bolstering your impressive three point shooting. Arenas will get you 6, Ford 7, Stoudamire (if healthy) 5 but Roy is a big question mark. I like to play (depending on roster size) with four guys giving me at least six assists.
As far as Tim Thomas and Jorge Garbajosa, you are going to get a crappy FG% from them so you might as well get some assists at the same time from a point guard.