Guys what’s your opinion on asking vtubers to say things? I’ve done it maybe three times since getting into Hololive and I’ve never asked them to say anything inappropriate but is it annoying to do that? I know Calli doesn’t like people asking her that so I’d never ask her but should I stop doing it all together?

It really depends on what you ask them to say. If they like going along with simple gags like funny requests then I'm sure you can get away with asking for goofy things but they can always decline to do so since it's their stream of course. Remember that they're all different in terms of personality with different ideas of what's funny and what isn't. I'm sure they've all gotten plenty of weird SuperChats that they didn't read out loud because they were inappropriate or strange.
Above all I trust in them to let chat know if something is bothering them or getting on their nerves.