The chances are the same with 1 and 2. 1/9 is a Thursday and after the big rush of post-holiday returns to the US, so I don't think the odds are terrible. But you probably won't know until shortly before and a single cancellation from the day before or another airline could pack it full. Also, a lot of people end up gifting expiring PlusPoints in January, which could hurt you since you could be behind some people who otherwise wouldn't be on the upgrade list (but help you if you are such a recipient who clears). I upgrade my wife and daughter (both Silver) ex-Australia when they travel separately from me every year or two and have pretty good success if it's into the second week of January.