OP heres my advise.
Take a long hard look at why you want to do this. Its a lot of time and potentially a lot of money to dedicate to one single hobby. The cars can't be used on the road and if you are get serious about it you eventually have to make a decision about going full time. traveling and all that come into play. In circle track racing the highest i would recommend going, on a hobby level, is legends, drawrfs or midgets.
Personally i have no affinity towards one type of racing over the other, but it seems to me that guys who do track days at mid ohio have the best of both worlds. Multiple classes, as much money as you want to spend, "race cars" can be street legal, and traditionally the most amount of damage taken will be self induced.