Here is a quick skill evaluation of Cutler from NFL Draft Showcase.
Analysis
STRENGTHS: Size, Escapability, Toughness
WEAKNESSES: Mechanics, Decision Making
NFL COMPARISON: Marc Bulger, Rams
Cutler and Bulger have similar builds. They both also have good arms, but their gunslinger's mentality leads them to make their share of throws they shouldn't. Neither are outstanding runners, but show good presence and manuverability in the pocket.
SCOUTING REPORT: Cutler has the tools to play at the next level. His college production and track record are more difficult to evaluate than that of other top QB prospects because he did not have a great supporting cast. His physical skills however, speak for themselves. He has great size and is a strong player. He has a good muscle base and an tall frame. Mechanically, he has to work on a couple things. He holds the ball low on his drop back (chest-level) and his release needs to be rasied as well. Cutler has had more passes batted down than he should and that can be attributed to his release. Holding the ball low on dropbacks as well as dropping it to his hip when rushed exposes it to rushers and also causes wasted motion in his throws. He has good natural arm strength and can throw the ball from many different angles. His passes have good zip and he can fit the ball into tough spots. He has the arm to drive the ball downfield, but his deep balls tend to hang and flutter too much. In general, he must do a better job of setting his feet and really driving the ball on all his passes. His footwork in the pocket though, is very good. He shows good ability to feel the rush and slide around it. He can make plays with his feet and while he isn't blazingly fast, he is difficult to sack. He can throw on the run, but will make some questionable decisions when flushed outside the pocket. He must learn to live to play another down. Accuracy wise he is solid and getting better with time. He throws the ball particularly well on crossing routes as he leads his receivers and allows them to make plays after the catch. Going along with that though is anticipation. Cutler must learn to anticipate and time routes better rather than waiting for his receivers to break and then releasing the ball. Part of his turnover problems are due to him staring down his first read for too long and releasing the ball late. As he progresses, he must learn to manipulate the defense with his eyes and come off to his check downs quicker. As a field general, Cutler has had to be the leader and the main man on some undermatched teams. He is a player with high character and high football I.Q. which bodes well for his future.
These evaluation of skills tend to be very critical of players. It seems the reason Vandy didn't have a very good team this year is due to lack of support players, not Cutler himself.