pshuang

I think there's also decisions to be made soon about awards that will only reach their 12-month post-expiration date fairly soon after the RR 2.0 epoch date as well as awards that won't expire at all until after the RR 2.0 epoch date.

E.g., suppose you currently have a Standard award that had expired on 03/02/2010. On 03/01/2011, after conversion to RR 2.0 rules, you will still have the right to pay $50 to extend it, but that will be your one-time final extension for that award. If you do exercise that right, you would then be able to fly on that Standard award until 03/01/2012. However, if you prematurely pay $50 on 02/28/2011 to extend the award, you now have a Standard award expiring on 02/28/2012 when the conversion to RR 2.0 rule occurs. On 02/28/2013, you should be able to pay $50 to exercise your RR 2.0 one-time extension right on your then-365-day-expired award. In that case, you should still then be able to fly on that Standard award until 02/28/2014. Of course I carefully constructed this example to be extreme. By spending your $50 a mere 1 day earlier and spending another $50 much later only if necessary (because you didn't use the award meanwhile), you gain nearly two additional years to use your Standard award.
I think this scenario is a no-brainer: people should go ahead and extend early in this scenario.

Let's move 12 months along the spectrum. If you currently have a Standard award that will expire on 03/02/2011, you could spend $50 to exercise your RR 2.0 one-time extension right on 03/01/2012, and fly on that award until 03/01/2013. Or you could spend your $50 a year early by extending on 02/28/2011. On 02/28/2013, if you still hadn't used the award, you could then exercise your RR 2.0 one-time extension right and spend another $50, and fly on that award until 02/28/2014.
This scenario is still mostly a no-brainer, I'd say people should go ahead and extend in this scenario. You're paying $50 in advance to buy the option of one more year to use your award, and yet it doesn't really cost you $50, because you would have had to pay $50 later anyway to use the award at all. And if you can't come up with $50 a year early, this probably isn't a game you should be trying to play....

Let's move even further along the spectrum by another 6 months. If you currently have a Standard award that will expire on 09/01/2011, now things get messy. If you plan to only extend once under RR 2.0 rules, you may have to spend up to $50 to be able to fly up until 08/31/2013. If you prematurely extend once under RR 1.0 rules and then plan to extend again under RR 2.0 rules if necessary, you spend at least $50 and up to a total of $100 to be able to fly up until 02/28/2014.
Now this is harder to figure out. If you don't prematurely extend, and you find an opportunity to use the award before its current expiration of 09/01/2011, you pay nothing to use the award. If you prematurely extend and you still find a good opportunity to use the award before 09/01/2011, now the $50 for premature extension is truly a sunk cost that you might have been able to avoid with perfect advance knowledge.

As you continue to incrementally move along the spectrum, the amount of additional time you buy by prematurely extending (and committing your money) becomes less and less, while the window of time during which you might have been able to redeem the award before its original expiration date and thus pay nothing in extension fee grows and grows. The extreme, of course, is a Standard award earned on the last possible RR 1.0 date, 02/28/2011, and expiring in 02/28/2012. Paying $50 to prematurely extend that award is obviously a pure waste of money, because essentially nothing changes. WN shareholders would thank you, though.

Personally, I'm thinking of using 09/01/2011 as a cut-off. Awards expiring before 09/01/2011, I'm doing something about them before the RR 2.0 epoch date. Awards expiring after 09/01/2011, I'm going to leave them as is, and if I need to, then I'll extend them under RR 2.0 rules. Also, something to consider is that if you do decide to pay under RR 1.0 rules to extend a bunch of expired Standard awards, that's an opportune time to consider the free conversion from two Standard awards to one Freedom award with the earlier of the two Standard award expiration dates -- you'll end up with a Freedom award with the maximum possible lifetime. Conversely, if you have several Standard awards that aren't expired yet but that you do want to prematurely extend, instead of paying two $50 fees to extend each separately, consider paying the $50 to convert two of them to a Freedom award with a freshly assigned expiration date. My intention is to have a basket of both Standard and Freedom awards as we enter the RR 2.0 era.