Steve,
If I read it correctly(maybe I didnt) on your 1st run you were shifting on the hills. I would very heavily consider against that in any condition. If by chance you miss a gear, youll have no jake and chances are wont be able to get it back into a gear the faster you start moving. Hotter brakes=more youll have to press on them to slow=no brakes.
This is me personally, I have never switched the jake. When your loaded low or medium is about useless. When is icy/snowy I turn it off, empty and wet/icy/snowy I turn it off.
If you switch the jake in the wrong conditions, it can be enough to lock the rear wheels, and spell trouble.
Also, thats why you cant sleep
Turn that trash filled CB off..LOL
Good luck Steve, The thrill of being able to do what you want when you want to do it, you cant compare it.
Good luck and have fun. Just remember about the shifting on a hill-its not a good idea. On a hill, or on train tracks.