Of course, if the user uses indentation at the first line,The true problem here is: I am such a user. :-)
There are also users who write lists after entries... and the default behaviour is wrong for them. I don't think it's needed to change their habits and force them to write a blank line.
I agree that it's difficult because it's not very clear where the metadata section (CLOCK/DEADLINE/SCHEDULE, drawers, …) ends.
Maybe it can be made that: a list (of any tipe) at line beginning (no indentation) will break the metadata section and start the content section.