I use comic shanns mono [0] for both printscreen annotations and in neovim with the hopes of subtly trolling whoever I'm sharing screen with.
For three years have I now suffered, with 0 reaction. Three years. I haven't lost faith though... one day, someone will say "what the hell kind of font is that? why would you do that?", and I will chuckle.
I appreciate your pursuit of this artistic endeavour. Truly great art is always the product of great personal sacrifice.
That said, it does make me wonder about two alternative approaches:
A) When a screenshot is detected, change the font, produce the screenshot and then change it back. You could probably do this on a per-application basis with something like AutoHotKey, or there's probably a deeper way of doing it on the OS-level.
B) Use the magic of AI. Given it's monospaced, you could probably modify an image model to replace the relevant font of the screenshot.
Of course, these approaches may compromise your artistic integrity.
As a typography dork who annoys friends by pointing out fonts all the time, it saddens me I am not your coworker to fulfill this long con. Much respect.
Monaco, which used to be the default font for MacOs, is my favorite. And it is a cousin of comic sans. It was designed by Susan Kare, one of the original designers of the Macintosh.
I extracted the TempleOS font (which itself was mostly ripped from FreeDOS apparently) and used it for all the text in my browser with a CSS override addon a few years ago:
For three years have I now suffered, with 0 reaction. Three years. I haven't lost faith though... one day, someone will say "what the hell kind of font is that? why would you do that?", and I will chuckle.
[0]: https://github.com/jesusmgg/comic-shanns-mono