I know I might be in the minority here, but I think extending Rondo before the season starts is a big mistake. Especially if that player is young and still kind of inexperienced like Rondo. I know Rondo has the makings of a great point guard and is very athletic. However, alot of people seem to forget that Rondo REALLY NEEDS to improve his shooting. Also, he is VERY tentative with the ball sometimes. Along the same lines, it seems like he tries to make fancier plays than he needs to. The job of a point guard is to keep it simple, be a leader and take the open shot when it's there. I don't know that any of this criteria embodies Rondo.
Now I am obviously rooting for Rondo this year to improve his game. However, I will not be heartbroken if Danny decides to hold off. Especially when you look at the amount of good free agents that will be available for 2010/11. And if Rondo commands more than 5/50 million after the season, then don't let the door hit him on the as* on the way out.