I would like to re-iterate that this isn't a "Problem".

I think that's a matter of opinion. It's certainly a nuisance that the UI's "randomization" doesn't behave the way you'd expect, and whether it is enough of a nuisance for an individual to classify it as a problem is up to them, don't you think?

Because that's really what this boils down to "Always randomize the contents" shouldn't just randomize its immediate children, it should randomize "everything in that playlist tree". It's not a "shuffle vs. no-shuffle" issue, it's a "does the option given to always randomize a playlist behave the way you'd expect it to", and I contend it doesn't. I'll defend that position by saying that even the guy who has access to the code thought it behaved as I did until he went back and looked at the code.

I don't see how it could get any simpler than that.

If you'd been paying attention, it could get simpler by not having to push that button at all.

D