SimpLESS is the perfect name, as the program works brilliantly in the background. I'd highly recommend it for both Mac and PC users.
Whether it makes you sad or not is irrelevant. What matters is what the users think, and if Reddit's reaction to it is any indication some will think it's funny and some will think the author is a bit of a dick.
I'm willing to bet that those who don't like it aren't Mac users.
Like mentioned above, these apps are programming tools. It's not like he's mass marketing these to uninformed consumers.
Yes, let's please make development less fun, more "corporate" and gray. Humor and professionalism do not match.
Humor is "the quality of being funny", and professionalism is all about "doing your job well". It's obvious that a funny FAQ messes with their ability to code a useful app.
There's nothing from with a bit of personality, but it's a tricky road when you're dealing with Apple products. There's a fine line between coming across as fun and a bit of a dick.