Originally Posted by gemac

OP - basically, you are asking us to weigh the chances of a comp upgrade, how important it is to you to be upgraded, and the chances you will find a better use for the eVIP for a trip in the future that you don't have planned now. It seems to me that you would be better positioned to make those judgement calls than I am.

GFRM - ROCK----->You<-------HARD PLACE. You have three choices:
1. Wait on the eVIP clearing MIA-GIG. If it clears before X upgrades start clearing SFO-MIA, no problem, you should clear both segments. If it clears after, you burn a SWU and ride transcon in the back.
2. Apply the eVIP to SFO-MIA and waitlist it MIA-GIG. If it clears before flight time, no problem, if not, you have burned a SWU and ridden in the back to GIG.
3. Pull back the eVIP and request the comp upgrade SFO-MIA. If it clears, you could then waitlist for the eVIP upgrade MIA-GIG, but you will definitely be at the end of the wait list. You won't burn the eVIP needlessly.

Which one should you do? Again, it depends on the importance of each upgrade to you, and the potential other uses for the eVIP.