>You can have great software without insulting half the internet
You overestimate how many web hipsters there are. And annoying them is not "being an immature brat". It is precisely to discourage their involvement. Because the mentality behind the web fads are precisely why the entire world of software is layers upon layers of shit stacked on top of each other.
libressl.org is the most professional landing page a project could ever have, what more do you want blink tags hero unigs, marketing spots, slideshows??
Every sentence and paragraph on that page is meaningful, unlike _any_ modern web crap app/mvp where visitor has to click and mock about just to find what the hell the page/project is about. Here its in the first sentence and you cant miss it.
And they could make it look decent by replacing Comic Sans with Arial, Times or something similarly simple. You can't tell me they used Comic for any reason but to annoy people.
May be you missed to read the footer of the page.. the last line, Infact they are also trying to make the same point as you said (why not use Arial or Times and get rid of comic sans)
With a PhD in architecture, design and branding, there's something about the extreme simplicity of OpenBSD's web pages that I find really attractive. "Perfection is achieved, not when there's nothing left to add, but when there's nothing left to take away".