Haneda from Hakone or Kanazawa or Takayama

During the last day of our Japan trip we have to catch a 5PM international flight from Haneda airport. I would like to know the best way to reach Haneda airport before 2PM from Hakone or Kanazawa or Takayama via train. I would like to minimize the risk of missing flight.

Either Hakone (close) or Kanazawa are not hard. From Takayama there are several routes, but all take a lot longer than the other two locations. Certainly for minimizing your risks watching for disruptions (by weather or otherwise) in advance would be advisable. As an example, my recent Kanazawa to Takayama trip took an hour longer than planned due to a passenger accident in Gifu prefecture (none of the prefectures I was actually travelling through).