I think the problem is that you did not give that task a due-date. Without the first due-date being set, it doesn't know when to schedule the reminder for. You need to give it a due-date in addition to the due-time, so that it knows which day to send the reminder.
The "repeat" value is only used to reschedule a task once it is marked as completed, it is not evaluated to guess at the due-date that you were intending. You need to enter the due-date explicitly.
What I condemn though is the cost of learning it the hard way.
Yes I understand your pain here and from other of your posts. Yes TD could be clearer. What I suggest to you and others who are planning on trusting TD with important tasks and reminders is to do some testing and experimenting before committing to your system and use of TD.
I still have a folder I label as "Exp" for experiment in which I create various kinds of tasks and subtasks just to see how they work for me. I know this is after-the-fact for you, but perhaps others can learn from your painful experience, and you can adopt the strategy for the future.
While I am not making a excuses for TD and its ease or difficulty of learning its behavior, Gcal as a calendar program that many rely on has plenty of quirks and difficulties. Trust but verify seems like a good approach.
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