I'd seriously consider keeping your day job, using half the $150K to buy a Pitts and get involved in competition Aeros and later on Airshow flying. Very rewarding, a type of flying you obviously enjoy, and I would suggest more financially practical than eaking out a living in GA at your age.
I wouldn't swap my job and the experiences that led to it for anything, but I got in early enough so when wife/kids/mortgage/dog came along I was established and earning a decent coin.
Much as I think my job is a great way to earn a living, if the big Loto win ever came my way I'd be spending a lot more time in an Edge 540 and an ASW 28 than I would be in a jet.