Your plan mostly sounds fine with rebooking over and over again, but travel funds have an expiration date which is the original purchase date, not the date of the original flight.
Will the travel funds expire prior to flight
#2 ?
Do you have to put in additional funds for flight
#2 ? Any new funds will be tainted with the original expiration date.
Is there enough time prior to expiration for flight
#3 if you cancel flight
#2 ?