Not saying what you did is not crazy, but I do think you should check out the EYW thread on what Cow did
For myself, I had 2 trips for EYW4 last year and my 2nd trip was started on a Monday morning at 6:30am from YYZ and return on the Friday (same week) at 3:40pm at YTZ, a total of 37 segments (I don't have the miles info handy) in 105 hours and 10 min, never left the airport, longest "scheduled" layover was ~4.5 hours.