PEBKAC: Reader failed to parse documentation. First thing is that I should have been passing data= and not files= in this call. Second, I misunderstood the following statement in the docs for RequestsLibrary:
data a dictionary of key-value pairs that will be urlencoded and sent as POST data or binary data that is sent as the raw body content
Specifically, I didn't apply the word "or" to the right phrases. Just in case someone else missed it too, it's "(A dictionary of key-values pairs...) OR (binary data)." NOT "A dictionary of key-value pairs or (a dictionary of) binary data."
I was going nuts trying to figure out why you'd use a dictionary of binary data. Too much time in strongly typed languages I guess. The key is that you can pass a dictionary when your POST data is something like form data, or you can pass a string (which you may wish to assign via the OperatingSytem Get File command). Once I realized I should be passing just a string value, all was right in the world.
Thanks to Bulkan for setting me straight.