I doubt that they outright intend this outcome; but I’d be inclined to suspect that ongoing exposure to sufficiently extreme environments(here in the intellectual sense) probably has a tendency to produce people who are calibrated to improve balance in context at the expense of a certain amount of wobble if considered in isolation.
There’s both the behavioral aspect: if it’s you vs. a deluge of spoon benders and faith healers and mixed woo enthusiasts many of them either not advancing novel positions at all or deep into distinction-without-difference territory it’s going to require patience somewhere between “extreme” and “downright machine-like” to avoid giving the opposing argument a little less of the time of day each time it pops up out of sheer weariness; and the pragmatic aspect: if you get too bogged down in rebutting claims that (at least by the the worse-faith elements of the group you are opposed to) can be made profusely and swiftly you’ll be Gish galloped off the field in short order.
I’d be pretty unsurprised if, as an individual, Randi hardened well further into default skepticism than would be desirable in an active investigator; it would honestly be rather more surprising and impressive if he managed not to. However, as a defensive reaction to an outbreak of credulity you probably do a better job of playing counterweight by going as far as is balanced in context rather than is balanced in isolation so long as anyone you end up inspiring doesn’t follow you too closely.
Had Randi managed to harden ‘skepticism’ into the First Church Of Skepticology; Orthodox, sure, he’d probably be at serious risk of deserving charges of having done serious damage to skepticism as a thing. As is, though, (my impression at least) of his legacy is pretty much entirely a popularizer of doubt in the face of certain flavors of credulity; and demonstrator of how easy and attractive some flavors of self-delusion are; not a serious influence on the epistemology of negative controls and experimental blinding or gatekeeper of Real True Skepticism except perhaps on certain corners of the internet.
People just seem like they are very, very, rarely large enough to, personally, be both the response to current trends that they believe is necessary and an exemplar of exactly the ideal that makes them believe that response is necessary.
