I just talked to a Southwest ticketing agent and she said they don't know when the new schedule will come out. It's a gamble either way. If you book the first part now and a great roundtrtip comes up later, you can't join in on it. Or if there is a great one way now, you can book it and get locked in, but the return might be higher. Her bottom line was that if you find a really great rate for one way now, book it.
I know that you have had good luck with rates by booking seperate one way trips, and even booking different carriers. That never used to work in the old days because the best fares were based on round trip travel. I don't know when things changed. I'm still in the old school thought process, so I wouldn't know what to do.