Right, now I can really see (and from other contexts of trying to wrestle with getting things to work with my setup, hugely empathise with) the issues your trying to solve and I think you’re spot on, it’s that tricky issue of speaking to specific user cases.
In terms of what you’re trying to achieve I’d aim for exactly the same thing 90m of material in a specific sequence, it’s just that the particular sticky points you’re negotiating haven’t ever come up for me - I don’t use shuffle and I don’t use Apple. The main thing I was thinking when asking after the point was just trying to understand it’s value.
The only real advantage I had in mind in terms of (my personal preference for) individual tracks is that they make navigation easier. If a user has a slightly different scenario than a highly fixed 90m walk were perhaps they might have cause to pause, they’d be able to go to the beginning of the previous sutta. Or, horror of horrors, if eg. they think “hey, this sutta isn’t really what I need to listen to right now” they can skip to the next one (I really admire your listening principle of just taking what comes, but equally see the benefit of helping users to find the right way for them at a given time).
I think we’ve both said that the ability download a playlist is a high priority. In terms of whether having them as one file is a high priority, I don’t think a sample of two is big enough to assess, but I would agree that building to one potentially not very common use case isn’t ideal. My answer: ask more people!