It doesn’t look like a list to me

Then the - weren't needed.

Maybe instead of people needing to apply exacting rules to accommodate an accessibility tech

1. Nah, writing a space the conventional way suffices: - SPACE list item. Even aesthetically, the plain text looks atrocious without a space there & worse when rendered.
2. The technology is fine, there was even a button in the toolbar. It's not that hard to figure out to anyone trying: there's a preview button & they can edit.

All anyone has to do is (1) follow regular convention or (2) use the technology. Getting this wrong despite the technology & standard convention is less a technology problem & more a user problem.

Edit: I understand what you both meant now: quotation dashes. They're less common in English, but still correct! Edited my comment above to reflect this. Thanks.

It’s not realistic for all users to follow semantics

Not realistic for users to write lists the normal way that doesn't look wrong? I don't know guys

-first

-second

-third

looks obviously bad whereas

- first
- second
- third

looks right. Then you see the rendered result in preview. You also had a button in the toolbar to create a list.

I don't think this is asking much.

If you weren't trying to write a list, though, then I don't know what you were doing & I doubt a chat bot will either: could you link to an example of what you were trying to do? For all you know, I'm a chat bot not figuring out your intent. No technology is about to fix PEBKAC.

I think the bottom line is if you write lists normally, then everything else including accessibility will turn out right without you needing to understand the intricacies.