Hi Greg - not a problem!
Firstly, all of your route is doable with the Japan Rail Pass. The Tokyo Monorail from Haneda is fully covered by the Japan Rail Pass so you should have no problems.
Haneda to Kochi is quite a trip! For that you'll be wanting Route 2 on this itinerary for the smoothest journey.
From Kochi to Nara I think I'd advise going via Kyoto and leaving your luggage at the station in a coin locker or hotel before heading out to nara rather than going to nara via Osaka.
Kyoto to Nagano is a fairly simply trip either changing at Nagoya to a Ltd express, or carrying on to tokyo and transferring to the Nagano bullet train. I think I'd just make this choice on how I felt on the day as there's not much in it :)
Nagano to Tokyo is a direct shinkansen bullet train hop so you should be fine there I think.
Hope this helps!