The common reaction when I don't wear makeup is "are you tired?" Or " are you sick?" Not exactly screaming and running away, but not particularly flattering.

Maybe it's because people are so use to seeing you without makeup they automatically get worried that you're not okay, it's not necessarily how you look. Maybe, I don't know, I'm not there, but that was my first thought!
And about the guys wearing makeup: Like I said, i totally get it for like the news because of the lighting, and for movies too.
But in every day life, for when you're just being you, around the house, or going out with your friends, or work (and not like the news or something), I just think it's a tad odd for a man to wear make up
unless it's for acne. But to me, having breakouts make up never worked for me, and always made things worse, it gunks up your pores and just makes it more miserable. So medication seems like the better option.
Anyway!
I totally agree about brushes, there honestly are better brushes out there. I've had some that are extremely itchy and low quality. But I will say that just because something is more expensive doesn't always mean it's better quality. You just gotta do some research.
As I've grown up I've realized everything takes research now. lol