The way medalion upgrades work is that the Platinum level customers can upgrade whenever they buy their coach ticket, gold 72 hours before their flight and silver 24 hours. Gold (which is what I am) can almost always upgrade, while silver is 50-50. The problem now is that there are a lot of non-upgradeable fares available and I don't have the balls to spend $400 for a ticket if I can get it for $200 -- even though my employer pays and he won't know the difference.
I flew from LAX to ATL one evening back in February on an L-1011 and all 36 first class seats were taken, while coach didn't even have that many pax.
Another interesting thing is that medalion members can upgrade on domestic segments flown by overseas configured aircraft, which have the Business Elite section with the big 60" seats. These are available on MD-11's 777's and 767-300ER's.
"In God we trust, everyone else bring data"