I fully agree with the broad thesis. In general, persuasion does not work by explaining to people why they're wrong. We just have too many defense mechanisms for that.

People do know their own situation well, though, and will respond well to clearly presented solutions to their problems.

I hadn't thought about the selection problem inherent in orange-pilling, but you're absolutely right that it's at least as likely to catch cultish parrots as independent thinkers. I still think the best possible converts are ideologically compatible folks who just haven't seen the light, yet. I suspect those people will stand out like beacons when met and therefor shouldn't be the focus of our efforts.

The lowest hanging fruit seems to me to be independent merchants, who may not care about bitcoin at all, but will consider using it as a payment option if they know customers want it.