Such a great trip! With a few moto mishaps.
Riding the moto on unpaved roads following bits of The Pony Express and Oregon Trails in the mountains of Wyoming. Where I had the fuel petcock fall off the tank when I switched to reserve. Since no parts were lost, the bike was repaired with the addition of some blue Loctite. Later the same day I had the headlight retaining ring shake it's retaining screw loose, resulting in the ring and headlight going missing. When I noticed, I pulled over to wait for my wife to catch up, since she was following me in her Jeep. She said she saw something that looked kind of like a hub cap go flying off to the side of the road at one point about ten miles back when I was still close enough to see. Unfortunately it was too late in the day and we were too far away to bother going back to look for it.
With the headlight still missing, I rode the unpaved roads along the Snake River in Grand Teton National Park. Probably illegal without the headlight, but had no issues. The road going back West to Teton Park Rd was quite fun and twisty, even more so as I was dodging the puddles that my wife was blasting through behind me.
West of Forks, OR I strapped an LED headband light to my bike and enjoyed mostly holding the clutch in with a mildly speed limit breaking ride down the West side of the McKenzie Hwy in Oregon. A bathroom break had my wife pass me, after catching up and over taking her I was informed that that light wasn't worth crap as she couldn't really see it in her rear view.
Driving on the Historic Columbia River Hwy was much too good to pass up riding the moto, so a standard round 12v headlight was purchased at Wally World and duct taped into place. My wife reported the light was much better from a distance. The road was good twisty fun.
Beach riding on the northern Oregon coast with the cheap Shinko 244 tires doing much better than I thought they would. Was happy to kick up a little spray and enjoyed carving back and forth in the looser sand. Many, many donuts were done.
Crossing the bridge from Astoria, OR into Washington was where things went bad. About 2/3rds of the way across the bridge the bike started losing power, the engine died and I ended up coasting the final bit of the bridge. I knew right away what happened, flagged my wife down and loaded up the bike. Later that evening I'd pull the cylinder and find yet another melted piston. I had brought a spare piston, but I couldn't free the aluminum stuck to the cylinder wall this time.
According to everything I've found for reference on my bike, I had it set to run a bit rich at sea level. Every time I looked at the plug on this trip it proved to be running rich. I had played hard on the beach for hours and it was rich. Cross a bridge and it goes lean.
Fast forward a couple weeks. Cylinder is cleaned and honed. Compression checks good. Fire the bike up, it idles for about a minute and dies. Fouled plug. Check spark, seems okay. Fresh plug same result. Clean plugs, nothing. Check points gap, hey something's wrong, as the breaker can move where it shouldn't. Pull the flywheel to get a better look. Another broken breaker.

Then it hits like a wave. I've melted three pistons. I've ended up with three faulty breakers, found after piston/cylinder repair. First one the heel's rivet had come loose, the other two had completely broke in the end. I don't have a carburetor problem. I've never had one. I have a problem with my ignition system going bad.
Question is, how in the hell are these breakers breaking? They seem to move freely enough. I've yet to see anywhere that they should be lubricated. I believe I still have a spare breaker available, but I really want to figure out a solution before I start riding the bike again.