Hart is a good player and has to claim the starting SF position, not just start. That's the only way I see him as a Blazer beyond this year. The fit beside Lillard and Simons is less of a concern, IMHO, than taking that position in no uncertain terms. With that said, like TINCE, I cannot see Hart on the Blazers after this season (and I do expect him gone by the trade deadline). His skills at both ends, the size of contract, and length of contract makes him THE player to trade whether in a significant package or alone. He has trade value. The back-up bigs need a serious upgrade in size with talent. The 3 needs an upgrade in size and talent. It goes through Hart. After Hart, it's between Winslow and Little with Little going out only in a significant package for a talent/size upgrade.
IMHO, the moves by Cronin, et.al. this summer -- GP2, Sharpe, and (to a lesser degree for now) Walker -- made trading Hart more likely as GP2 brings the D, Sharpe with better size and ceiling, and Walker with size and the beginnings of a multi-skilled, high IQ player. [The high value acquisition of Grant as a starter should solve one ongoing problem.]