iiiiinteresting. How are you saving the Start time exactly; you are saving time, day and month ?
I would try two things to start:
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rather than including “sorted by” in your data source - I would just put “Search for appointments” as your data source, then specify that it is being sorted by “Dynamic data” - Search for appointments start/time - descending = yes
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Same as 1^ - except play around with Dynamic data being: “Current date time (minus) Search for appointments start time” …
I’m not sure what the answer is yet. I know sorting a Repeating group by created date is very easily doable as a default function - and all that is is a date/time data field. So the sorting should recognize a custom date/time data field in the same way…