Just called back and they tell me I am on the list but it doesnt show up on pda so I am still not happy. I feel like cancelling the flight and just buying a new one but it's a $900 H non-refund.

You gotta love these lines the CO agents use to blow off customers. As far as I know, phone agents have no access to the airport upgrade standby list. He must've been blowing you off to keep his average call durations low.

This one also doesn't make sense. How could you be not checked in if you have your boarding pass?

call co.com support - that has always fixed it for me!

I have tried everything and hopefully my latest effort worked. I changed the flight from this week to next (need to be in Dallas anyway). I have now purchased another ticket for tomorrow's flight and if all is well I will check in and get on the upgrade list. Like I said I wouldn't care but they don't have any seat assignments for this flight so an upgrade would be nice. FC has 8 open seats as of right now and I should be close to the top of the list.

It worked.... Although not as good as I thought. I am a plat on a now $1,000 H class ticket and I am 3 on the list with 8 open seats. The good thing I was able to assign myself a seat but it's a middle exit row. Thanks for listening.... I am really upset with CO support and I wish they would have done more.

Happened to me, too
 

This happened to me in the first part of the OP.

When I checked in, both co.com and the pda site showed that I was in seat 1-E. However, my boarding pass showed "CHECK IN WITH GATE AGENT" (original in all caps). When I got to CLE, I showed this to an agent in the PC and she said she had never seen this before. I was indeed not checked in, although I was holding a boarding pass for the flight. She did some kind of override and handed me a BP with my seat assignment and informed me that I was now checked in. This was 40 minutes prior to scheduled departure.

:confused: