I wanted either UAL or SWA simply because both have a domicile where I live. I wasn't successful with Hogan, and SWA hired me a couple months later, so here I am.
I was wondering during my first year whether to keep my application at UAL active and retake Hogan. I chose not to for the following reasons:
1) I was already based where I was living, so that became a wash.
2) I've made it a point to learn to maximize my income at Southwest considering I live in base and can work out pretty nicely. In 2017, as a part first year and partly second year FO, I worked 185 days total in 2017 (by choice), and my W-2 was 170k. I managed to max out my 401k, with NEC contribution and profit sharing, I reached 415c limits, which for the current mil folks means I reached the IRS defined maximum allowable retirement contribution of $54,000 for 2017, and I'm getting an excess check in a couple of weeks.
3) I don't really care about flying a heavy or "seeing the world" consider I've flown literally all over the world in a corporate setting beforehand so that's not something I really care much about.
4) One of the things I was concerned with at Southwest was the relative lack of retirements when compared to the legacies. After almost 2 years on the property here, I'm in the mid 80's percentage-wise on the master seniority list. Upgrades are right at 60-61%. Based on projected hiring, mandatory retirements and not accounting for early-outs, I'd say my soonest upgrade will be right at 6 years on the property, or 4 years from now assuming the current trend continues and no major economic downturns.
5) Some of the other considerations... Southwest has the strongest balance sheet in the industry (can be a worry item actually), does not outsource flying, and has been historically profitable through some of the worst financial rollercoasters that plagued the airline industry.
When it's all said and done, my advice is go to the first one that hires you, and if you have a choice, live in base. It's a completely different job if you do for the better.