According to Daniel Negreanu to make $50k per year you need to have a minimum $15k roll and play 30/60. He also said you have to be a darn good player to do it.
My suggestion to you T-Park would be to read as much Sklansky as you can, and also read Jennifer Harmon's section in Super System II.
$500 per day is $125,000 or so a year.
Also, most of the good poker players have gone bust once or twice in their lives. Those are the few that come back from going bust, the rest and I would argue the majority of people who go bust become degenerate gamblers.
I would recommend the tournment route where you can controll your loses without it affecting the way you play. In cash games you can't play scared which is hard to do when you're on a very bad run of cards or luck. You absolutely need brass balls.