Lifelong Bronco fan here. The odds are very good that Denver got the best of this deal. Here's my own take on Cutler's skills:
Pros: Young, Good size, Has some escapability in the pocket, Can throw it on a frozen rope, Very cocky/confident, Has diabetes under control, Gets along well with his young teammates, is willing to run it hard and even throw some blocks.
Toss in that he is reunited with 2 former college teammates and goes to play for his childhood team and those are nice bonuses. The excitement of adding a borderline Pro Bowl QB will energize the fanbase and sell tickets. Jerry Angelo can't pick 'em in the first round anyway so were the picks a big loss? Jay is worth a shot here because with proper development he has a lot of upside.
Cons: He's a punk bitch, Sulks when the game isn't going his way, Has a good Jay/bad Jay way of playing - when he is off he doesn't pull it together during the game, Can only throw it on a frozen rope - lacks the touch to loft it up and hit someone deep, Bad field vision, Seems to decide who he is going to throw to and when before the ball is snapped (quadruple coverage anyone?), Doesn't look a safety off of receivers, No pump fake, Pathetic play fake, Lacks accuracy as he frequently throws either behind or high and those Chigago winds may make that worse, When he runs and blocks he has a baaaad tendency to lead with his throwing shoulder and head, Crappy agent, Has yet to show he is a gamer.
Want to defend him? Get your hands up at the line of scrimmage and try to keep a defender between him and the receiver = Pick City if the Linebacker/Secondary/Lineman

can hold on. Chicago's O-line and receivers are worse than Denver's. The Bears have a proven history of not developing QB's and I have the impression that Bears faithful don't like pussyboys. He's awful with the media and they will turn on him.
I would have liked to see what was possible with McD and Jay over the next 2 years and didn't like the idea of him being traded a month ago. However, Cutler has proven over time how big of a bitch he is and how little desire he had to be a Bronco. He had to go and the Broncos got a lot of value in the trade. Our D was the worst in the league and 9 first day picks over the next 2 years should go a long way towards strengthening my team for years to come.
We'll only know how this pans out in 4-5 years. I think Denver got the best of this but
if Jay elevates both his game and personality and if McD can draft well and develop those picks, it can be a win/win for both squads.
Orton & Simms? I don't know. Orton (21-12) sounds like a good guy who tries his best and Mike Shanahan loved Simms' potential. May the best man win. At the least we got a good backup for many years. System QB's don't have to be Elway and I respect McD's track record there.
I can't wait for the season.