Here's what I do when I book travel ... I go to Expedia and put in the time and date I need to fly and click search. I then sort by departure or arrival time, depending on which is most important for that given leg, then I select the most reasonably priced flights for my desired departure and/or arrival times. If Southwest also flies the route I'm flying I'll then check and see what they have to offer for the route. Then I buy the ticket that offers me the best combination of price and desired arrival and/or departure times.

Elite status is nice ... but in my experience, it's just not worth much compared to saving money and flying on a convenient schedule. Besides, with the alliances these days you're likely to end up with elite status anyway, maybe not top tier, but enough to get you good coach seating at least.