excellent post; I’ve been using Priceline for years. Depending on which country I’m visiting the US site or the others are more appropriate to use and hence I have several profiles. Comes in handy also if I’m in a rush and need to bid more than once a day 😉
In addition to the websites suggested, there is one direct competitor to PL (which might give you further hints on areas, availability etc): hotwire.com. They are now even advertising rates comparing themselves to PL!
The other obvious workaround to the one-a-day is to start bidding well in advance! With a bit of discipline, simply upping your bid by a dollar every day will get you a deal eventually.
One remaining challenge where I am looking for suggestions: how to avoid the Hilton Chicago (it’s in the Magnificent Mile zone with many of the other nice hotels), its so in need for a refurb.