I thought it was weird to NOT look! Last trip I waited patiently for the 14-day mark and was astonished to see the last minute deals window not move to cover my dates. I checked a couple of days before realizing the page was cached and I needed to refresh it for the new dates to show up! OOPS
Southwest fares and car rental rates are something I tend to get obsessive about eeking out the best deal possible, so I check rates every day. It isn't so much the money as the "game."