Thanks for the tips everyone. I've gotten pretty used to the bidding strategies using Priceline/Hotwire so that's not an issue at all. Having flexible dates helps us quite a bit there too.

Priority Club seems to be getting the most recommendations, so I'll definitely look further into their program. Out of curiosity, with all of the promos stacked, how many points can you generally earn per stay?

I'll probably do the Priority Club card a few months down the line...too many recent Chase applications (BA and CO in the past 30 days) so I doubt they'd give me another one anytime soon.