I'm sure there are many with Southwest here and en route who will welcome you with open arms. But if you don't find joy in answers to your specific question, you might try looking over on the Hyatt Gold Passport board for the thread, "Clear - is it worth joining?" The Gold Passport program has had a promotion for members to get a Clear membership, free for a year. I don't remember if or how it's targeted. Otherwise, it costs [$100 or $128]/yr. But you will probably save much more than that flying on Southwest. (In my view and others', this would have been much better co-marketed with Southwest. Case in point: You.)
http://www.flyertalk.com/forum/showt...t=clear&page=3
By a year from now, or from whenever you might join, some of the things in the news might be implemented -- e.g., three lines up to security, one of them "Expert". The reports say TSA wants it, not a bad omen. Hopefully, Expert will not equal Clear (pay to play).
As to your tool situation, I've found that on Southwest there's usually a lot less luggage checked, and bags come up a lot quicker. (I don't know how this compares with the former Air West part of US in the southwest.) Moreover, just as Southwest announced its policy of charging for three or more bags, the other majors began charging for the second. Another good reason for your choice.
Finally, there was also a rumor on this board, I can't remember how substantiated, that the RR card works for using the elite line at some airports. But it may be a long shot.