dakkon
I found this to be a decent watch forum. I bought my CW watch used from here for around $200 shipped.
http://forums.watchuseek.com/forum.phpIf you get onto the CW mailing list, they will send you codes and notices of secret sales. There is one going on now for the existing C5 since the redesign is about to be released.
For a boutique brand, in the year I've been watching it, it's held it's value well.
Also, don't get too caught up on the band style. You can always change the band to leather, cloth (NATO), rubber, steel, etc. I do that on my Binnacle and it allows the same watch to have a different look just for the cost of a bracelet/watch band.