I'll kick in on the gearing for the WRR. The two of us ran 14-47, and doing it again I would use 14-50. Spring for a Ironman rear sprocket! You just can't wear them out on a trip like this. Don't go to the 13 front as it puts the chain too close to the swing arm. Several have found out the hard way! I also bought a DID X Ring Gold chain and never needed to adjust for the trip. Amazing. We all lubed our chains every morning, whether they needed it or not. As to gearing, yep, California Pass was the only place where first gear was maxed out after making the final switch-back. I never stopped, but the revs were way down and there wasn't a half horsepower to spare. The 50 would have made it a breeze. The other thing is that the 50 will let you use third gear a lot instead of winding it out in second. Lots of places where that happened out west. An option would be to change sprockets when you get to Colorado, or in New Mexico. Lower gearing is not needed until then.
Fuel Pump. Both of our WRR's were 08 models with the original fuel pump. I had no problem, but the other one would get hot and stop. Letting it cool down solved the problem and I think that bike is still doing fine. Mine just finished 2500 miles on the Forever West route this September, and developed a problem along the way. Whenever the gas level got below the pump, it would heat up and provide much reduced flow. Within sight of the finish line, literally, we had to stop and add fuel to the tank to get it to work. I've since replaced the pump with the revised unit and expect no problems for a while. I read very recently that BigDog is now on his third pump having replaced one not long ago. It's really too large to carry on the trip, but it would be a good idea to buy one and have it handy, all boxed up, at home or a friends so they can overnite it to you if needed. Otherwise, the WRR seems bullet-proof.
Carry a spare oil filter, and some pre-oiled Filter Skinz. The latter are great as you can just pull the dirty one off and slip on a new without having to go thru the drill of cleaning and re-oiling the main filter. Lots of dust out west! Check often in NV or you will be loosing a lot of horsepower from a choked engine.
I carried a spare clutch cable taped to the frame, up behind the seat, and to the frame on the other side. Didn't need it but I wouldn't be without a spare. Routing it and having it ready to go would be smarter.
Another item that I really liked was the Wolfman Carry All, hooked to the bars and resting on the headlight fairing above the lens. Very handy for things that need ready access. They come in two sizes and I use the small. I have the large on my Husky. 'Don't know if that will work with the Lynx, but check it out. It puts just a few more items up front and off the rear.
Enjoy the trip; I'm going to do it again before long, the West that is. We routed around just a few areas due to weather or time, and I want to put them all in the bag.