Apologies... I might have missed something here...
Six years and no answer? I think this is an essential feature in order to use shuffle with classical albums. Anything???
The bold bit... I'm not sure about... I have seen many posts reporting unexpected behaviour with random play, however, my own experience is as I would expect.
These days, the majority of my listening happens in the car, connecting my phone to MC using JRemote. The various playback options I have set are almost all of the "pick some genres, discard anything played in the last seven days, and shuffle". I never delve into the file lists in JRemote; too fiddly in the car. I just long press the title tile and hit "Play all"....
In all my time doing this, any time a file with links has appeared in the randomly shuffled list, the entire linked set plays as expected.
More thinking out loud...Does it have to be the first linked file? The end goal is to have the full linked set in the list?
I'm also thinking, expansion is unnecessary, surely, because, if you made the list so that it contained just one linked file from each linked set, when you begin playback, MC would automatically expand to include the rest, because, they are linked. No?
Anyhoo, lets see...
A smartlist using the rule:
-[Link Start]=[] ~limit=-1,1,[Link Start]
I would have expected this to return 1 file from each linked set, which could then be sent to playing now and thus, auto-expanded, but that is not what I'm seeing...
Here, I see MC is automatically expanding the linked sets and including them in the list, so, the question is, does this give you the list you require?
-marko.