Some great points. Whatever "system" the White Sox have in place has to be the cause. That's painfully obvious which makes it even a scarier thought. I'm sure they've tried to iron it out - but there really must be a major disconnect there.
Could it be that noone in the organization knows how to develop position talent at any level? Is there a single person in-house who has a modern day philosophy that is proven to deliver results? If not, no amount of talent is going to fix this mess.
I think what's probably more the case is just hopelessly optimistic talent acquisition. Buying a guy at his peak value doesn't seem to pan out. You have to take those risks to get a guy who may have turned a corner towards consistency - but it just seems to blow up in the organization's face over and over again.