I think this is fair. I'm fat, queer, and disabled. My (neurodivergent) son calls me grandma and it's funny because I know he means it lovingly. However, if my boss decided to do something similar, I'd spit in his eye. It's a case-by-case basis.
Make fun of Caitlyn Jenner for being a entitled, right-wing murderer? We're good. Make fun of Caitlyn Jenner for being trans? We've got a problem.
Who is saying it and the intention behind what they're saying matters quite a bit.
Not even then, I don't think. I'd sooner write-in Vermin Supreme, as would most people in Chicago. Luckily (?), the city is the reason why Illinois is blue. Go an hour away in any direction and you're in enemy territory - but an entire town out there has fewer people in it than there are people living on my block. So, it works out.