This is a really interesting topic to me, because I've felt a pull toward things like this myself and seen it for decades. For example, the top of the README in my Zephyros project[1] was very playfully done, and very well received too.

People are naturally more lighthearted and organic than the sterile software and documentation we tend to write, and we're more social too, wanting to connect with others even if it means through a simple in-joke or catch phrase.

[1] https://github.com/sdegutis/zephyros

I am not saying to not be human and take all the zest out of the writing.

FWIW, I suggest the book On Writing Well. William Zinsser has valuable advice on how we can still retain humanity in our writing without being dull and lackluster when dealing with dry and "sterile" topics like software.

Part of nerd culture finding it's next level will be we stop saying "next level".

Memes are the next level, it seems

It certainly was in 1994.

https://www.wired.com/1994/10/godwin-if-2/

An army of trolls that launch a fringe reactionary political movement which transcends the national boundary with postmodern "dank memes" seems to be the level we are at now. I wonder what's coming next...