It looks like you are learning along the way and that's the fun way to learn. Like you I worry a lot and as soon as I get rid of one worry I find something else so I can relate to what you are saying about that.
Years ago I spend 6 months doing what you are doing, it was the best and I'm enjoying reliving the travels through you.
I hope you end up out in the NW during your journey, it's a great place to ride and I would enjoy the chance to meet you.
Keep riding and keep enjoying what you are doing.