I'm flying ORD-FRA-MLA in a couple months and am trying to upgrade on the ORD-FRA segment (on UA...FRA-MLA is on LH). I have UA Gold status. I know that once I submit the request I won't be able to see cash upgrade offers. Since the timing of when you submit the request is pretty far down the list of factors UA considers, it seems it would be better to hold off on requesting and monitor the cash upgrade offers until a week or two before flight. Then, if the offers are still too high, submit the upgrade request and hope for the best. Right now the upgrade offer is $2300 for PP and $4600 for J, both of which are absurd.

I would of course prefer Polaris but PP would be fine too. I'm currently in E+. It's on a 787-10. I also know this is fairly business heavy route but I'm hoping a Friday night flight won't have too many full-fare-paying people on board.

Does that make sense? Is there something I'm missing?