I don't think we are that far off either, meaning the players needed to make the next jump are easier to obtain than the players we have. Lillard, Batum, and LMA are good. Wes and JJ are solid players right now.
Leonard is exactly what we thought he would be this year, a very inconsistent rookie who needs time to develop. But if he stays healthy there is no doubt in my mind he will be a good center in a couple of years.
After that we have a bunch of role players that are OK..... if they are playing with starters. Not so good if they are all playing at the same time.
So for right now we could use a really good back-up PG so Lillard can get minutes at SG.
In the off season we need to upgrade the SG spot to a player who can create his own shot. And also secure the back up PG spot.