Assuming you could make 20%/year net of fees, commissions, etc, you'd need a bankroll of $250k to make $50k/year. Of course, you woudn't be building up your equity at that level so I'd say the minimum you'd need to be a self supporting trader who can live on $50k/year is $500k.
As for...
R is an outstanding programming language that will enable you to test any kind of strategy you can dream up. It is free, well documented and well supported. Highly recommended by this humble trader.
The hottie who was interviewing him was wearing a giraffe print dress which no doubt got the mad wild jungle Cramer frothing at the mouth. But this was a staged performance as evidenced by his eye cues to the girl both mid way through and at the very end.