Is one who broke their fast while traveling from Saudi Arabia to Canada required to make up those days, given that they knew breaking the fast was permissible during travel but did not wish to do so, then later broke their fast based on the advice of a friend who cited a prophetic hadith, and then broke their fast for three days after arriving in Canada due to not being settled?

If you break your fast while doubting the sunset, you must make up that day, whether it later becomes clear that the sun had not set or not, because the default is that the day is still ongoing. However, if you are predominantly certain that the sun has set and nothing indicates otherwise, then your fast is valid.

Regarding breaking the fast during travel: If you intend to stay for four days or more, it is not permissible for you to break your fast, and you must make it up. If you intend to stay for less than four days, or you are undecided, it is permissible for you to break your fast, but you must make up those days in any case.