It's called one time per level of nesting -- one time with all top level groups, and then one time per group (at any level) with its nested examples and groups. It doesn't split things by file at all, unless you organize things so that you have one example group per file.
And to clarify a bit: to RSpec, files only have meaning in that they are what it loads. Once it's loaded the spec files it deals only in the in-memory example groups and examples, and reording files isn't even a concept that would make sense.
Myron