Run it once, a month before the season starts.
Find everyone who came last season and did not come back.
Message them the new dates before they go on sale publicly.
Note who books so we know the early list works.
Two weeks later, message everyone who did not reply, once.
These are instructions for the assistant, carried out one at a time against your real records. Each one still goes through the same checks as if you had asked for it yourself.
Once you have an account, ask for "Season opening" and it is added as your own recipe. From then on it runs on your records, not on an example.
Run it on every enquiry, whatever channel it came in on.
The money timeline for a dated booking.
The week before. Every question they were going to ask, answered first.
The message that turns a no-show into a rebooking.
Run it when a date is close and under capacity.
Same day or the next morning, while it is still fresh.