I would be pretty confident in betting the Jazz dont draft Sheppard or Dillingham. Ainge's draft history is pretty clear. He likes size and if he's drafting a shorter player they have to have some combination of length, girth, and defensive tenacity (think the smallest guy he has ever drafted in the first round has been Avery Bradley, 6'3 in shoes w/ a +4'' wingspan at 180 lbs).
There will just be too options for players in the same tier that have size for Ainge to pass up on to draft Dillingham/Sheppard.
Terry Rozier is 6'1" or 6'2" and around 185 lbs, but he was also a mid-1st rd pick. Also, the game has just evolved and length and athleticism on the perimeter are really sought after.