The bit about Millsap's next contract is a big thing I've been wondering about. These max deals for these older players are pretty brutal. I suppose it's good for the players but it's going to lead to even less players ever playing for just a team or two. I think it sucks though because it makes you put a huge unfair bet on a veteran who deserves credit. Millsap was amazing last year I thought as a true two way player and it sucks his team has to think about trading him because you have to bet on him for 5 more years. But that's the game I suppose.
But to me the Wade move was a sign of that already happening. Did not see that coming.
Honestly overpaying for players like these at their age group is not going to cripple you. What cripples you is giving high salary in multiple year contracts (even max contracts) to what essentially amount to role players and just above role-players.
All-Star types & near All-Star types you can gamble on quite comfortably, particularly when you consider how low your chances are of acquiring top talent without even factoring in how your chances drop substantially if you don't already have skilled talent in your team.
That said, considering the cap jump next season, and the subsequent cap drop, next year will be a Summer of a lot of potential costly mistakes, and this includes giving a chunk of money to those near All-Star levels.
The other side of it is, the alternative of doing nothing is just as bad. It's a gamble either way. Thankfully, the C's are in a position to do both routes at the same time. Things are getting a touch complicated, but we still retain a lot of cap flexibility going forward, and even with all the picks we used up this Summer, still retain A LOT of them going forward.