1) I understand LeBron didn't want to duplicate the career arc of Kevin Garnett. So why not sign a six-year extension in 2007 that would've kept him in Cleveland until 2013? He'd be 28 in 2013, and if he still hadn't won a ring, he could go somewhere else with his prime intact to win a championship. Jordan didn't win a ring until the age of 29. It's ultimately his choice where to play, but I don't think Cleveland deserved to lose him at this stage of his career.
2) Everybody makes the point that LeBron didn't have that #2 option in Cleveland, that he was surrounded by a bunch of decent players, but he didn't have his #2. Well, by not signing an extension that went past 2010, it complicated efforts to put together a good enough roster. They couldn't get younger players that could grow into their roles over time, like the Bulls did when they traded away Oakley and gave the starting job to Horace Grant. Or by taking a very green Scottie Pippen and patiently waiting for him to develop into that #2 option. By having a 2010 deadline, the Cavs had to construct a veteran, le-worthy roster on the fly. Plus, they had to run everything by LeBron, personnel-wise. He bears a large amount of responsibility for the roster he was surrounded with in Cleveland.