You won't have to worry about running wot all day. My groms engine has spent 90% if not more of its life in the red line and I'm getting close to 14,000 miles without an issue or any noises from the crank bearings. I do have a kitaco clutch cover and takagawa oil pump, no cooler yet. Last summer my temps avg 240*f on long wot runs, one time saw 264*f on a super hot day on a long wot run up some canyons.
I'd upgrade the stock chain so you arn't adjusting it every 300 miles. I did a 428 chain conversion on my Grom and love it. Hasn't needed an adjustment in 3,000 miles so far.
Pack up a small tool kit that lets you do basic maintenance. Here's my tool kit(I took the wire tool out and replaced the bubble wrap with a small rag). I can do anything on the bike with it and the sockets(17/19mm)/ratchet under my seat aside from changing a tire, only have half the tools I want for that at the moment.
I also run a product called "ride on" in my tires. It balances them and will plug most tire punctures.
When you do the trip keep us updated! I'm interested in hearing about it!