Yes. With that in mind, we should go after Jarrett Jack as a combo 1/2 bench player. What are your thoughts?
I think it's heavily dependent on the draft.
Under contract next year we'll have the following under guaranteed contracts:
PG: Lillard (38mpg) , SG: Wes (35mpg)/Barton, SF: Nic (38mpg)/Claver, PF: LMA (38mpg), C: Leonard (~20-25mpg, whether starting or not)/Freeland
We also have the rights to Printezis and Papanikolou (who are assumed to come over).
The cap hold for those players is $45,201,378 (including the 4 roster holds to bring it to 12). We don't have to worry about the "minimum" threshold (90% of cap, or around 54M) b/c we're still paying Roy's amnestied contract for 17.9M or so. Assuming the 9th pick (about as low as I'd reasonably expect) the cap number will be 46.9M. With the 12th (the "highest" pick we can have) it'll be 47.2M.
So if the cap doesn't change from this year's 58.044M, then we'll have a minimum of 11M in space, and maybe up to 13.2M. Stern's been putting out that revenue projections are way higher, so we may have much more space. Add in Hickson's 7.6M cap hold (and remove one minimum roster hold) and the numbers become 4.9M - 6.1M in space (with maybe a lot more).
Like I said, though, the draft plays a big part (I won't even delve into the trade deadline scenarios which would make all of this moot). Assuming the 9th-12th pick we're in range for McCollum, MM's Fave Mike Carter-Williams, Trey Burke and Marcus Smart (maybe). Each one of these might be capable of pulling off 10 mpg or so as a backup PG. However, if we choose to exploit the depth of big men in the class (right now it looks like someone like Poythress, McAdoo, Gobert or Plumlee should be available, then we're at the same place as if we didn't have a pick--needing someone to play 10 mpg of backup PG. Someone like Telfair or Shaun Livingston or Krypto-Nate or Earl Watson should be able to do so while being almost vet minimum. Jack will probably require more than the MLE, which is why I'm holding off on him for now. You also have to believe that he's not just having a career year shooting 3's (42% right now) but that it'll be sustainable. I'm not there, yet. If you got past the brain issues, Tyreke might be the guy to throw half of the wad at to play PG/SG/SF minutes off the bench, but I'm not completely sold on him yet, either. Boobie Gibson is also an option for a 4-6M/yr contract that might work if you're going for high-rent district, b/c he's a very solid 40% 3pt shooter.
The reason that I'm looking for an elite one-dimensioinal (shooting or D) SG/SF rather than someone like Jack is b/c I'm a believer in Nic's playmaking skills. Much as Paxson and Kerr and Ron Harper could play PG with Pippen on the floor (not saying Nic's there yet, but he's getting good at finding the open man), I think that someone like Tony Allen, Morrow, --or, if you're looking bottom-end, Corey Brewer, Dunleavy, Nick Young (even Webster

-- could be out there with Nic and not flail around for 10mpg. However, JJ Redick is getting to be my perfect image of a backup SG that can play PG (his assist rate jumped up to 25% this year, and he's getting almost 5apg). And we know he can shoot. I think that if Lillard/Wes/Redick play every rotation minute at the guards, then we're doing alright --except maybe on D if we go with Lillard/Redick for long periods of time.
Then again, it's looking more and more likely that two types of big men will be available. Guys like Howard (maybe, but probably not coming to POR), Bynum, Pekovic, or Jefferson for the big money and junkyard dogs like Turiaf, Blair, Nazr Mohammed. I'm a bit biased, b/c I think there are 3 things you can't have enough of on an NBA team...perimeter lockdown defenders, elite 3pt shooters and rebounding/hustle machines.
Apologies for the tl;dr (that's what you get for asking for "thoughts"

), but if I was going into the offseason with the most restrictive scenario (no draft pick, 13M in space) then I'd probably let Hickson go and hang on to Leonard, Freeland, Papanikoulou as my bigs and maybe add one of the junkyard dogs for relatively cheap (2-3M). I'd look to throw a 4/34 or so contract at JJ Redick (starting at ~8M/yr), maybe sign one of the cheaper PGs (Robinson, Livingston, Telfair) for insurance and then get Babbitt on the Room Exception (2yrs/5.3M total). That gives us:
Lillard (38)/cheap PG like Robinson, Livingston, Telfair
Wes(34)/Redick (25)
Nic (38)/Babbitt (10)
LMA (38)/Blair (15)
Leonard (24)/Freeland (12)
If you keep Hickson's cap hold, then you're down to about 6M, which doesn't get you Redick or Allen or Tyreke, IMO. But you're still looking at splitting that money on guards (with Hickson staying with LMA, Freeland, Leonard, Papanikolou we don't have minutes for someone like Blair or Turiaf) in something like Morrow and Telfair or Gibson and Robinson--none of whom move the needle.
Again, that's a worst-case, most-restrictive scenario.