Are there any guidelines on how to name roles?

Nope, I tend to do a lot of "WithSomething" and "HasSomething", but only when it makes sense. I am really not a fan of the Java/C# interface practice of prepending an "I", so I would not suggest the same but with an "R" unless you like that practice.

I think the "does" comes from the Perl6 keyword. But in Moose the keyword is "with", so that confuses things a bit.

The reason we have "with" is that since that is really just a function, it would conflict with the "does" that is found in Moose::Object which is used to tell if something "does" a role $object->does(My::Role). I would have preferred to have used "does" and be more Perl 6 compat, but I had to work around the Perl 5 limitations.

FWIW, the "with" keyword comes from Scala.

So, any good ideas on how to think or phrase the description of names for classes and roles?

Not yet really, although I haven't given it a whole lot of thought. I am sort of waiting to see, as the group of people using roles grows, what patterns (actual patterns, not GoF patterns) begin to develop for usage and naming. At this point myself and nothingmuch have probably been using roles the longest (at least in Moose) and we each have our own approaches (see Forest and Bread::Board for examples of my usage and KiokuDB and Class::Workflow for examples by nothingmuch).

I guess to not answer your question more clearly,.. there are no rules :)