I don't know what my personal record was, but I received plenty of different notifications for one flight (when storms were rolling through the airport) as follows:
Departure time +35m
Gate Change
Departure time +55m
Now Boarding (and we actually boarded)
Flight Cancelled (no crew)
Flight Reinstated (they found the crew that were on board the aircraft)
Departure time +15m
Departure time +30m

Flight eventually did depart 2.5 hours late, luckily I had an 8 hour connection (which ended up departing several hours late as well for unrelated reasons).