Your posts in this thread have been wonderfully insightful, and have helped me to crystallize my own thoughts on this topic.
I'd just like to add another item about the Reinsdorf-owned Sox: Not only has the franchise not won enough, it doesn't believe in the value of building a minor league system. That is an organizational philosophy straight from the top; JR doesn't believe in making premium investments in prospects who haven't "proven" anything yet. So, we take the cheapest route possible in building our system. It isn't a coincidence that the only sustained period of success during the Reinsdorf era came from the efforts of the Himes regime. Instead, we rely on dumpster diving -- looking for bargain free agents and hoping they pan out. Usually, they don't; with 2005 being the glaring exception.
Part of the way fans develop a passion for their teams is by following their minor league prospects as they develop. It gives the fans a greater sense of identification with the players as they roll through the system, and the bond with them is strong once they reach the majors. Of course, we have had relatively few prospects worth following the past decade. Many of those who have developed have been traded away.
In sum, we don't believe in building from within, and we won't pay top prices for premier free agents. What is left is the steaming pile of mediocrity that is the JR Sox. Like I said in an earlier post, I can no longer support this franchise with this owner. It's difficult to say this, as I've loved the Sox with all my heart since 76. But the bottom line is that this is entertainment. This is not life and death; it's baseball. And if following this team makes me miserable because I fundamentally disagree with several key principles upon which it is run, the onus is on me to change my behavior. I certainly do not expect JR to change.
I live in Dallas, and my son loves the Rangers. For years I've tried to steer him towards the Sox, but he finds their games "horrifyingly boring". He always has. Even though the Rangers suck, he'd rather watch them lose 10-7 than watch the Sox win. I'm learning to embrace his thought process, and enjoy the game of baseball with his team rather than worry about the perpetual incompetence of my own.