The overarching problem you outline in your second paragraph - the more general problem, faced in many fields, of having to compress a degree into a few sentences to properly answer an objection - is sadly well known. This is why the RationalWiki article (which is still patchy as heck) is a sea of nuance and caveats - it attempts to get it right in less than a book for an audience who are frequently just realising that there's actually historical thought on this matter (and look how that line of inquiry worked out for Lukeprog!). I'm very much looking forward to Richard Carrier's book on the historicity of Jesus later this year. (And not just so I can crib furiously from it.)
To break up the awkward silence at the start of a recent Overcoming Bias meetup, I asked everyone present to tell their rationalist origin story - a key event or fact that played a role in their first beginning to aspire to rationality. This worked surprisingly well (and I would recommend it for future meetups).
I think I've already told enough of my own origin story on Overcoming Bias: how I was digging in my parents' yard as a kid and found a tarnished silver amulet inscribed with Bayes's Theorem, and how I wore it to bed that night and dreamed of a woman in white, holding an ancient leather-bound book called Judgment Under Uncertainty: Heuristics and Biases (eds. D. Kahneman, P. Slovic, and A. Tversky, 1982)... but there's no need to go into that again.
So, seriously... how did you originally go down that road?
Added: For some odd reason, many of the commenters here seem to have had a single experience in common - namely, at some point, encountering Overcoming Bias... But I'm especially interested in what it takes to get the transition started - crossing the first divide. This would be very valuable knowledge if it can be generalized. If that did happen at OB, please try to specify what was the crucial "Aha!" insight (down to the specific post if possible).