I'm guessing this may simply be one of those things only an analog delay can do, but I'm curious to know whether any digital delays can do the time-stretching thing without getting all chirpy and glitchy.
yep! add the dd-2 to that. you can also pitch up/down the "hold" (sample) mode of the of the DD-2/DD-3 by turning the time knob.dd3/5 does not glicth, it pitches up and down like an analog delay
Alexander History Lesson II is programmed to eliminate that when you turn knobs or tap a new tempo
The original History Lesson does have the pitch-shifting artifacts and the History Lesson Vol. II does not. We got dozens of emails from V1 owners complaining about the pitch change, and then when we released the Vol II we got dozens of emails from players complaining about the lack of the pitch bending!