If you're going to use Southwest, in addition to booking all of your flights online, I would also use Hilton & Hertz. At Hilton (including Embassy Suites, Double Tree & Hampton Inns) you get HHonors points for the stay and 1/2 Southwest credit as well (see Hilton section). Hertz will also give you a 1/2 credit per rental. Also look at the Southwest Visa, you get 1 credit per $1000 spent. So you can earn one free roundtrip for every 3 trips - the best domestic deal going IMHO. if you earn 100 credits in 12 months, you get a companion pass for one full year. This allows a designated person (can be changed 5 times during the year) to fly along with you for free.
Also check out the Hilton forum and learn how to get comped Gold Status (also get the Starwood - Sheraton & Westin - comp too).
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Ken in Sacramento