I can't answer your exact question but can give some insight into the civil aviation side. I have a non-aviation bachelors, a great job, and part ownership in a Mooney. My commute is 17 minutes, I don't have to worry about TSA, or long periods away from home. I fly when I want to and as often as my wife and checking account allow.

My employer permits me to use my plane for business trips and I am partially reimbursed for that. I can't expect them to pay extra for my "hobby" when a commercial flight will get me there cheaper. I gladly pay the difference, because it's like free or reduced cost flying hours.

I'm very happy with my situation. I have 1000 hours TT in 17 years of flying, which I assume you would find to be a drawback.

Good luck on which ever path you take!