I'm actually doing most of the things you suggested, CSC...
The 'when' is kinda something I need to get specific on, like 'if this happens: yes, if this happens: no'...
Currently I have NO caches other than my stores.
First I'm going to have to get specific about the final destination of the trip, then I can plan routes, more safe houses, and caches.
How I will get there is pretty much answered; vehicle, animal or foot... in that order.
I have Stores prioritized. If we take 1 vehicle we take highest priority supplies, but we plan to take a vehicle with a trailer, which will hold all of our stores (everything from brand new clothing, to ammo, guns, propane, stoves, files, tools, books, sleeping bags, tents, boots, food, water etc.).
Who I will need to contact isn't much of a priority, as my family has already been informed of the general area I'm going to, and my unit is too small to warrant contacting anyone.
The BoB s are under construction...

How exactly do you prioritize routes to a new AO for Caching?