Ditto. I've been checking on upgrade (using miles) CLE-IAH-GUM-CNS for the past 4 weeks; each call, I get different information/answers. We leave Wed. I have a horrible (for me) waitlist story that will have to wait till I get back. Briefly, they upgraded me CLE-IAH, but say that IAH-GUM doesn't look promising. If I take the CLE upgrade, I automatically get charged the entire miles for the upgrade (25K). If I decline it, I'm taken off the waitlist, and I have 0 chance of upgrading at IAH. Its even more complicated that this.
Unfortunately, this type of thing seems to be very common.