>>>>>In both cases, I aborted OLCI the first time and came back several hours later.
More great info. Here's the final kicker:
Suppose you check-in 24 hours prior and have two segments. You get asked if you want to upgrade to first. You say yes. On one segment you are told that you are upgraded to first class. For the other segment, you are told that First class is full and you are being put on the waitlist.
If you then abort, and try again a few hours later, will you still HAVE the one segment that cleared in first class (i.e. that upgrade will "stick"), and then it will still be possible to snag an F seat that crops up on the previously unavailable segment?
I know this is arcane, but it makes for a very optimal decision-tree!