Waitlist unreliable for mileage upgrades--be proactive!!!
I have two upcoming trips to OGG, both returning on Sundays. I like that it only takes 17,500 miles to upgrade three flights (DEN-IAH, IAH-LAX, and LAX-OGG), so I went ahead and upgraded both itineraries. In both cases, the final flight back (IAH-DEN) on Sunday afternoon was waitlisted.
I have been checking to see if "R" availability would open up on those flights. The first one opened up two days ago, but I was still showing waitlisted, so I called the elite line and the agent got me the seat (he mentioned that it was R1 only...glad I called in). This morning I noted that R was available on the second IAH-DEN flight, but when I checked my reservation, not only was I still in coach, but the waitlist was gone! The agent was perplexed by that, but got me the FC seat (it was also R1).
Moral of the story: Sometimes one's obsessive-compulsive disorder pays off. Watch your waitlists like a hawk and monitor availability, or you may end up in the back with no cheeseburger for dinner.