Originally Posted by evergrn

I've never stayed at Andaz. You'll have to sort of make the decision on which property to stay at in Tokyo and how to make the best use of your points. To me, Hyatt Regency is a fine choice. Little more convenient than Park Hyatt with respect to distance to train, shops.

$400-500 could get you into a lot of fine ryokans in Hakone if on a weekday (Sun-Thu that's non-holiday). For high-end places possibly in that price range during the week, look into these:

http://www.gorahanaougi.com/hanaougi/
http://www.kyuan.jp/
http://www.hakone-kamon.jp/

These are all very highly-regarded. I've actually only stayed at the first one (most of my stays have been at second-tier places), but I always have my eye on onsens in Hakone and those other two are high on my list of places I'd like to stay at eventually. Hanaougi may not be available for $500. Usually more like $600-700. Of course, dinner & breakfast included. Private en-suite onsen in your room. The other two places are a couple notches cheaper, usually. There's plenty of places that are more like $250-300/night for two, but still decent and relaxing although not super-luxurious.