I’m an OpenBSD developer (mostly a packager). IMO you’ve mischaracterized both Theo’s response and OpenBSD’s culture.
If OpenBSD has a culture, it’s not “real men,” but “show me the code.” That’s plain from the mail linked in the post you responded to: mailing lists are full of people making suggestions (like “rewrite OpenBSD in Rust”), but few people doing the necessary work (like implementing or testing a reasonably POSIX‐compatible userland, handling the 8+ architectures that would immediately have to be dropped, measuring the performance impacts on the project build clusters…).
Contrast the above response with the WireGuard implementation this whole discussion is about. A non‐OpenBSD contributor sent a draft patchset, which received suggestions and was iterated upon several times, and despite some complaints about the concept from one quarter (https://marc.info/?l=openbsd-cvs&m=159273877612032&w=2), it was committed by the very person who had those complaints! In the end Jason and Matt of WireGuard described the process as “extremely pleasant” (https://lists.zx2c4.com/pipermail/wireguard/2020-June/005588...). This is feedback I see often from external contributors.
You describe safety guards like privilege separation and pledge/unveil as “real men programming”, but they’re the complete opposite: they exist precisely to mitigate the damage that results from human error. acme-client’s design does keep private keys inaccessible this way (see https://kristaps.bsd.lv/acme-client/). Privilege separation is a proven technique. OpenBSD is not a project that says it’s okay to live dangerously as long as you code with the right macho attitude.
There are plenty of valid things in OpenBSD to complain about—it might even be valid to argue that our resistance to Rust disproportionately values architectural concerns over memory safety!—but don’t blame “real men programming.” That’s just false.
I am baffled as to why you attribute OpenBSD’s ACME client lacking DNS challenges to this same “real man” attitude rather than the simple reality that in a relatively small, completely volunteer project nobody has yet done the work to integrate that feature. If someone sent a patch to add dns-01 support—certainly something very useful that plenty of our users and developers want—I bet it would be committed within weeks.