Having grown unschoolers, we have a unique vantage point. We're past the point of speculating and hoping everything will work out. The kids are grown... grown-ish (are they ever REALLY all grown up?)
Here are a few blogposts that address some of the issues that we faced or are facing now. Feel free to ask questions in the comments - I'm happy to share what worked, what didn't, and what I learned. Hopefully these will inspire you and/or help you along your own path.
Black & White? Or Gray? [a follow-up to Should You Unschool?]