That bit was both hilarious and terrifying.

Hilarifying.

Didn't she also have moments like this in early seasons as well? (this counts more as "innocently insensitive," but pointing out Cranky's baldness to everyone only for the town to laugh at him was a little bit dickish)

I think the main thing with Pinkie is that she's sort of the character where, if an episode focuses mainly on her, she's portrayed very positively and fun loving, making everyone love her. When she's NOT the focus, the writers feel like they just need to give her SOMETHING to do (sometimes even if it's just a very brief moment, like in Twilight Time).

Eh I admit sometimes it can feel a little off putting to see Pinkie's character almost change dramatically in some episodes, making her feel inconsistent, but I guess maybe that's the point. She's Pinkie Pie, and she's weird. [my two cents on the matter]