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It sounds like you're asking, "How do I fuck my life up without fucking my life up?"
I suspect you know there isn't a simple answer. You have to decide whether "flipping the trips" is really what you want to do with your life, or if you've got higher aspirations. And if you do have goals, then you need to restrict your drug use in a manner consistent with achieving those goals.
You say you have an addictive personality and that it's all-or-nothing. If this is the case, you really need to stay away from benzos. Unless you know of any productive job/goal where being barred out of your skull isn't problematic.
Hard drugs can be used while leading a productive life, but it's never an easy balance. Usually the most successful hard drug for productive lives is amphetamine, but even then you need to moderate in order to minimize getting spun and crashing.