One thing about the SWA hiring process that isn't totally obvious...
You want to keep your SWA application current, however SWA will only post the job opening during brief application windows once a quarter or so. During the window they'll build a list of interview candidates, then pull the job listing until the interview list is depleted. SWA projects pilot hiring to continue throughout 2019 at a pretty snappy pace so even though the pilot jobs aren't posted right now, they will eventually open up the application site and you'll want to have your app ready to go when that happens.
As for your personal timing... SWA has a career expo coming up in mid-Feb, which tells me that by the end of Feb they'll have the job posted and open for applications. If you have a friend who works for SWA *AND* you meet the minimum requirements right now, get your application submitted and have your friend recommend you for the career expo before the end of Dec. Any number of hours at that point would look better than zero.
Reasonable options for you could be to get a guard/reserve gig asap and separate as quickly as possible, get hired by skywest or whatever regional, while you actively apply to SWA. Any movement at all towards securing yourself a flying job should look good to any HR panel because they know that your future flying career depends entirely on your intent. If you want to fly and take steps to get a flying job, you're going to be flying somewhere almost without any doubt. So just have proof of that intent (a class date with a regional, a guard job, a regional type rating and a few months as an RJ FO, etc) and it should show you are determined to make it work. That matters.