The Obie teams didn't just fall apart on their own, they were dismantled purposefully. Maybe because they were "fool's gold" and didn't have a real title chance, but it's not like the core just stopped playing well all of a sudden (yes, Walker proved himself to be an inefficient chucker, but he was that anyway, it's just that Pitino leaving and Pierce being the better offensive player got him less focus so his box score started showing it more). And yeah, it's too bad they traded Joe Johnson to bolster that 2002 team, but, bear in mind that with the same essential core, they showed a bunch of improvement after ditching Pitino, and the team was in a bad place after the Pitino years anyway. With hindsight you soldier on with what you have, sure, but without it, I make that trade every time. (Too bad the Suns weren't high on Kedrick Brown instead though, right?)
As for this year, I am and was fine with standing pat. They are basically playing as expected. If Durant had come here or if Brown had been an instant All-Star I would agree about pushing harder to improve in the right now but I don't think there is any need to pay an inflated price just to get something done because Love's injury makes the Cavs more vulnerable.