I think the permaculture people have a lot of good ideas, but they're a bit too much back-to-nature and anti-technology for me to be entirely comfortable with.
Regarding Paul Wheaton in specific, a few days ago I learned about an experiment he's doing called "ant village," and I've been reading up on this with great interest. He set aside 12 one acre parcels on his property, and invited people to come develop them for a couple years. The challenge is to see who can make the most progress in the allotted time, building a shelter, growing food, etc. There's a lot more details that I'm not going to try to explain, but you can read up on it over at the permies.com forum:
http://www.permies.com/forums/f-102/labs. There are also journals from some of the people participating in the challenge.
It wouldn't be for everyone, but this sounds like a lot of fun to me. You get to start with a completely natural bit of land, and see how much civilization you can build up in a couple years.
Relevant to this forum, Paul mentioned that he expects many of the "ants" participating this challenge to have a residual income stream while they're doing this, and even mentioned ERE at one point. So I assume he's well acquainted with the idea of FI.