David, thanks for the reply!
If it should work consistently, then I'll dig in and try to figure out why it isn't for me. In my experience this works reliably with an empty track and an empty project. But in other cases (already a midi clip on the track, other tracks in the project) I've experienced:
It works. Cakewalk plays prior loop passes while recording.
It kinda works. Cakewalk plays prior loop passes, but the midi notes double up on the second pass through, triple up on the third pass through, etc. (Earlier passes get louder and flammed. When I stop though, it goes back to single notes.)
It simply doesn't work. I can record multiple takes on a single track in loop, sound-on-sound record, but I don't hear the prior takes until I stop and restart the recording.
As far as I know, I'm not doing anything exotic with the tracks. The one I'm recording on is doing "Input Echo = Auto Thru", all other tracks not involved in the recording are on "Input Echo = off".
If anyone knows of a tutorial, youtube video, etc, on how to do this reliably, I'd love to see it!