In case it helps:
I can say that I never, ever,
no matter what, and there are no exceptions
- make a list like this
I always
- make a list like this (I happen also to always indent by 2 spaces)
IIRC, org-list-allow-alphabetical is default nil largely to avoid
making a list. IMO doing so by requiring a blank line (at least
optionally) before lists would allow that variable to be safer.
IMO it is a lot to expect of users if they paste large documents (or
even capture them as part of org-protocol or something), and there are
plenty of filling edge cases, such as illustrated in the recent thread
about filling with > and filladapt, where you'd have to either check
manually every time you fill or actually hack the filling code to
understand list syntax.
Just my opinion, though.