Added a few more edits based on comments above. Also a few comments.

Insurance is probably a whole string in itself - though it is also going to differ by country. Considerations I've looked at include (a) taking care of things while on the trip, including potential evacuation coverage in case of severe event (b) requirements to maintain insurance within USA (c) what mix of providers and reputations.

Many packing lists out there as well as discussions on them. Here is mine for my upcoming trip: Equipment - A bicycle ride across the Americas Fortunately, I also anticipate on this extended trip I can send things away and get new ones if necessary. Probably the biggest thing I'm doing differently here is expect that the Dalton Highway at start is likely to be my coldest (i.e. warm clothes), most remote (i.e. extra food, not much power to charge electronics) as well as first place to start. So I'll start with necessities there and send a general delivery package to Fairbanks for things I won't need right at the start.

Something else I've done, but not sure fits exactly in the checklist is read whatever journals I can to learn from others experiences in similar places. It gets me excited (and sometimes worried ) on the trip, but also finds some good nuggets of information as well.