Mellow - Hard to comment on all your questions, but overall, sounds like you've thought it through. Only suggestion I could make would be to do the southern route out, northern coming home. We hit snow (light/wet) crossing the Bighorn Mts in WY 2nd week in June in 2006. Of course, I don't know the mountains , and that could have happened several days later, too.
The H&B bags are a great idea, I modded up a mount for the small Givi E21 bags, and my riding bud was using much larger Pelicans or similar. Probably close in size to your H&Bs. In any case, a set of hard bags turns the Bonnie into a lightweight touring bike.
This link will provide some photos of our two Bonnies, outfitted somewhat differently.
http://s115.photobucket.com/albums/n...;20Out%20West/
The major difference (aside from different handlebars, saddles, windshields) was the fact that my 'minimal' Lucifer Orange and Silver T100 was equipped with a RenTech rack which I used to carry tent, sleeping bag, and air mattress. My buddy used large soft bags bungeed to the passenger portion of the saddle for those items. I couldn't do that, since, with smaller hard bags, I needed the passenger space for clothes, etc.
Re the one person tent .... it doesn't leave you a lot of room inside for the rest of your gear (things like helmet, leathers, etc .... if you can find a lightweight 2 man tent for the trip, it'll leave lots of room for storing gear at night.) Both tents in the pix were two man.
It is difficult to account for all possible problems. We lucked out .... bikes ran perfectly for the entire 5000 miles, both got close to 50mpg running the two lane roads where we spent most of our time. No flat tires .... we left on new rubber, by the time I got home, the rear tire was fairly well shot .... it was a Dunlop 501GT. Front was good for 2-3K more miles.
One thing you may want to do is drop in at local libraries along the way and keep us posted about your trip. We did that, and several of the Forum members let us know if we had any problems, they weren't too far away.
Best wishes for the ride of your life! Once you're back home, you'll never look at the little Bonnie the same way .... you'll know she's capable of taking you anywhere.
Bob
PS - maybe consider taking a spare H4 headlamp bulb, and a brakelight bulb. I've had to find these things a couple of time when on the road.