From this seat, the obsession with the off-season should be on getting better, not younger.
As Roy has pointed out before, we need to add quality veterans who can bolster a championship run next season. If younger means "low risk, no upside" players like several of those we added last summer, then I want no part of that. The kind of help we need isn't going to come from the draft, and you're not going to find it in the dumpsters around the league, either.
TP to Jon above for an excellent point: There was a high level of serendipity in the events of summer 2007. Two clubs looking to dump stars for pennies on the dollar. Danny didn't have any dollars in his pocket, but he had a bunch of pennies and the two clubs sold out to him for change. Right place, right time? Yes. But lucky, also.
I'd like Ainge to ask himself this question before each and every signing this summer: "How does this guy help us win a championship this year?" If he does that, he won't sign the O'Bryants, Miles, etc.