You make some great points.
I rarely use WordPress.com and the last time I did I was disappointed to see it diverging from .org in ways that undermines its value to preparing people for .org.
WordPress.com’s UX used to be close enough to .org’s UX that it gave me an initial education that helped quite a bit when I went to self-hosted .org installs.
There’s so much to learn with .org beyond the basics of .com that it made a huge difference in enabling me to become fully committed to WordPress.
Now I can’t suggest people check out .com and see what they think before going further.
And that’s a real loss for .org. Not so much for .com.