Okay, this should be much easier to do now.
- Add `Multiple Mode` option to schedule items editor and remove support for count values of zero
- `Count`: same behavior as before, requires a number of media items to play and will always schedule the same number
- `Collection Size`: similar to count of zero before, will play all media items from the collection before continuing to the next schedule item
- `Playlist Item Size`: will play all media items from the current playlist item before continuing to the next schedule item
- `Multi-Episode Group Size`: will play all media items from the current multi-part episode group, or one ungrouped media item
If you select Chronological playback order and Multiple with Multi-Episode Group Size it should do exactly what you want, assuming you have proper metadata/titles.
For example, if you have episodes titled A, B (1), B (2), C, D (1), D (2), D (3), the first four times the schedule item was used (e.g. once/day on different days), it would schedule like this:
Day 1: A
Day 2: B (1), B (2)
Day 3: C
Day 4: D (1), D (2), D (3)