You're right, everything in life requires risk, and you never know until you try.
So go jump off a bridge.
C'mon ... oh, you don't
know you're going to die until you try it!
Well isn't that just a cop out, though?
Risks are not all created equal. Some risks are worth taking; others are sure to turn out badly. Running off into "the wilderness" alone, or while civilization is still growing, is no more a "risk" than jumping off a bridge. You
will fail, just like the long, long,
long line of people who tried it before you.
Does that make rewilding useless? Of course not! You can make yourself a little more feral every day without buying into the Romantic nonsense of running off into "the wilderness." (And, as I said before, just using the term "the wilderness" should raise a huge red flag that whoever said it doesn't understand what they're talking about.) Because if you're becoming more feral every day, and civilization is tipping a little more every day, then you're eventually going to reach the point where that risk tips, and then it's time to make a break for it.
So if you believe in rewilding, is it a cop out to pursue rewilding thoughtfully, effectively, in a way that will work, when you could make a suicidal break for it and get crushed? No, I don't think it is.
Fenris, your plan sounds an awful lot like mine. I guess you're copping out, too.

That approach is sensible, but following that won't have you running out into "the wilderness" any time soon.
Ando, you sound as if you think community is just a great thing to have. That's a very civilized attitude to have, the kind of attitude that gets you killed if you try to wander off into "the wilderness." Ask a native person, and they'll tell you the exact opposite: the community is
all that matters. Living in civilization to keep your community? So what, at least you still have your community. No native would
ever think it a good idea to abandon their community for "the wilderness," no matter what kind of mess their community was in.
Of course, the lone outdoorsman striking out into the wilderness is the icon of Romantic mythology that stirs the Western imagination, so it's hardly surprising to hear it invoked and yearned for. But pursuing that gets plenty of people killed, because it's a myth. That's not how native people lived, and out there, all the civilized notions you never knew you had will get you killed.
Did you hear they're making a movie out of
Into the Wild? That makes it onto every primitivist reading list for good reason.