Justin,
You really know how to set yourself up for disappointment. You've picked 2 incredibly difficult fields to succeed in. My advice is pursue the art and flying both. Your odds are better of having some success with 2 endeavors. If you want to have a satisfying flying career you should look into the Air National Guard. Otherwise be prepared to be happy on 50-70 thousand a year. And hope it doesn't get any worse.
I've flown civil and with the ANG and currently fly for a major. I will be lucky to make captain before I retire assuming I am still employed in a year. (My second furlough is looking like a real possibility.) For job security and a pretty good income, the ANG is the way to go. If you are lucky you can get a full-time position with your unit or stay a traditional guardsmen and continue to pursue your art.
You will hear a lot of positions on your dilemma and some will encourage you but if you do choose to pursue only flying, trust a pragmatist and be prepared for a long and frustrating road with the real possibility of no significant payoff for all your hard work.