Well it's still kind of cute? XD
So first stupid question: does the cloth object have thickness? (asking because I can't see it's too quick for me)
Other questions which may be relevant is what's its wireframe like (generally for cloth you want quads as square as possible, and more is generally better but also computationally expensive) and what settings have you been messing around with.
The second gif is hilarious, reminds me of a sim I unfortunately didn't render out where when I was just starting to learn cloth dynamics (I'm still learning), the pants on the character I was animating ripped themselves off the character and condensed into an angry ball that writhed in the air for a second or so before launching itself at the camera XD
I was using solidify with -0.1 or -0.01, does thickness matter that much? :D. I used the plane with 50 of the thingies when you spawn in an object, my terms with blender are not that good yet so hopefully you get what im saying haha
It does seem to need some thickness to work properly :)
50 of which thingies? There's a lot of thingies XD