The lesson to be learned with Cutler is this: If you have a quarterback who can do some good things, but hasn't proven beyond a shadow of a doubt that he's the long-term guy, you don't give him fully guaranteed money for more than one year in a new contract. Had the Bears simply made the 2014 salary a full guarantee, then "guaranteed for injury only" for the next two seasons, they would be in better position.
The Bengals did that with Andy Dalton. The Niners have done that with Colin Kaepernick. The Bears didn't do it with Cutler. Now they're in a "damned if we do, damned if we don't" situation.