I know I made a jokey-type post about this, but just FYI this is consistently not working as I'd expect it to. Maybe my expectations are off.
What I'd expect when setting "Keep tracks in sequence when shuffling" is that always - in any context across the entire program - these tracks will be considered as one. Always played together for an auto-playlist, always played together for a playlist mixer, always played together in Auto-DJ.
What I used to do in these situations is rip the tracks as a range in EAC and then make up a title for them, skip a track number or two in the album sequencing, and let that be that. Observing the original track numbering and titling seems much more "correct," but that only works if playback cooperates.
If I'm off about how it's supposed to work I can go back to one big "Golden Slumbers Medley" or "Brain Damage / Eclipse" file, but I'd rather keep albums as they were intended if at all possible.