Originally Posted by Chewie
Yeah I know. But, I haven't purchased it yet.
OK, in that case, the best (and really, only) way to "improve your chances" are to buy a higher fare class ticket.
Truth be told, I fly down to SJU about 6 times per year. In the past 5 years I've only NOT been upgraded twice (not too bad).
Not bad, I assume this has always been as Gold elite? Has it been on the BF-equipped 757 ever? Just so you know, this aircraft has one of the worst ratios of FC-to-coach seats in the CO fleet, so the statistical odds aren't in your favor. But if there are that few elites on this route (or they are flying with non-elite family), then you're probably in good shape...
Nothing better than discovering new toys.
Be careful, it's dangerous!