The economy will figure into things, but figure Rondo's next contract to start next season when he's 24 with 4 years experience and go for 5 years or so. In the middle of the contract he'd be 27 with 7 years experience. How many of those $8M-$10M players are better now than you'd expect Rondo to be then? How many of them are significantly better than Rondo is now?
Frankly, at this point I don't know what to expect from Rondo's development, but in four or five years, I'd still expect him to be outside the absolutely elite PGs, but still in the top ten. In other words, pretty much (in relative terms) where he is now.
After watching him improve over the last two years I'd be shocked if he's no better when he's 27 than he is now. Is he that far outside the norm for younger nba players? I can see why you're so lukewarm on his extension. I wouldn't pay him a fortune if I thought he's hitting a plateau now.
Well, as mentioned, it's hard to say. For instance, in some areas Rondo regressed last season. His overall jump shooting declined last season, and his FT% was lower than in his rookie season. For his to reach elite status, I expect his eFG% on jumpers to be better than 2nd worst among starters, or his FT% to be worst among all qualifying PGs. However, nothing to date suggests that Rondo actually will improve in those areas; we're just hoping he does.
It's almost always the case for younger players that their shooting and ft stats go up and down from year to year. It's not regressing. In fact it's extremely rare for players to not have those ups and downs. It's also far from unusual for younger players to struggle from the line.
Honestly I think you get a little hung up on some of these numbers. His overall jumpshooting declined last year but if you checked out his hotspot numbers for a given range over the two years there wasn't much of a decline from any given distance, but it had to do with where he shot from. Similarly, his fg% from a given distance isn't that far off from most of the best pgs. If you check out the difference between Rondo and Parker on 82games and nba hotspots you'd see that most of the difference between their jumpshot efg% is which of their shots from a few feet from the hoop were considered jumpshots vs inside shots.
Having said all that, even if he's never the best jump shooter (the way, for instance, Parker isn't) I'd still expect him to get more consistent over time (like almost all other players do) which would, in itself, move him farther up the list.