I think I finally found a really likable episode. After writing the above wall of text, I did a youtube search on "funny my little pony". Probably should have done that at the start.
Nearly all of the video was clips that, although were amusing weren't really funny, but at the end they showed only clips from an episode featuring fluttershy as a fashion model. Now THIS was funny. I don't think I laughed out loud at any of it, BUT I don't always actually laugh when something is funny.
Okay, so if anyone else beside me in the same boat as "I don't get it" (looking at you Instantdeath), let's check this whole episode out.
Green Isn't Your Color
I'm going to watch it now and report back when I'm done.