Your options are too widespread... You need to determine what sort of riding you want to do first...
However, given your experience and the new found adventure bike bug, I'd probably get a motard and a set of dirt wheels. If you want to blend all of your options, ditch the street legal idea... get an absused smoker... fix it up, trick it out, and take it to the track as a motard and to the trails as a dirtbike. You get the project, the nimble track bike, a fun dirtbike, and something to keep you away from The Gap.
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