I believe that your first question coincides with the following issue:
is there a way to specify DocBook indexterm attributes (like zone, range) in Asciidoctor?
Not at the moment. You'd need to extend the converter or use custom templates to add support for these additional attributes.
BTW, I know neither Ruby, nor Java, nor DocBook, yet I'm producing PDF's! That too on Windows.
Asciidoctor packaging is just terrific!