have some bail out points if it becomes to much and see how ten hours feels during daylight. Then learn what hazards there are along the rest of the route that could be a problem at night. Then do some shorter section with good bail outs at night to be sure. I personally have a policy to not do any land or water wilderness journey without having done the same route by day to understand the hazards.
But otherwise after doing some homework and testing things out a bit it seems like a doable trip at the right time of the year with good conditions.
Kayak Motor Kit
EZ-Dock modular docks
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