@capnm,
I have a vague memory (someone correct me if I'm wrong) that the special Collections, all by author and all by title, may not have been added to the calibre driver for PRST1/T2. It was a special feature added to the original Sony driver (PRS505 to PRSx50) by calibre developer chaley. I believe Kolenka did all the calibre work for the PRST1/T2 driver.
I also seem to remember Kolenka saying there was something odd about the way the T1 handled sort fields, hence the unpredictability of sorting the main book listings. I think sorting within Collections is done by the calibre driver, i.e. it works! ... as long as you sort by Added Order