I think at some point you have to decide to blow it up, and if I'm the Bucks I might have some concerns about not being able to get value w/ Bogut if he goes through another injury.
They're not just tied up financially, but tied up for quite some time.
I agree. That financial situation is really ugly.
Who, I have two problems with your plan. One, you are preparing for a day with financial wiggle room that is about 3 years from now. Considering Bogut's injury history I think it's a dangerous roll of the dice to expect him healthy at that time. Also, he will be 30 years of age at that time which means he will then be on the down slope of his career that injuries have already taken a toll on.
Two, what incentive do free agents have to sign in Milwaukee other than money? I can't imagine that Jennings, two young mid-late lottery picks, and Bogut is going to be that stunning of a cast to get any superstar to come to Milwaukee, Wisconsin at a discount. Preparing for that day of financial freedom, IMO, is preparing to overpay somebody and get right back in the same mess.
I think they need to build through high draft picks. They tried with Bogut and it doesn't quite appear to be working out. I think if they can get good value (draft picks or young players) for Bogut now, take it. Then losing Bogut will also drive their win total down giving them more good picks to build through in the upcoming years. It's pretty clear it's a roll of the dice to keep Bogut because they aren't winning any titles now and if he gets injured again, they might suddenly lose a lot of value in what is presently a pretty solid asset.