I would bring:
1) a tablet or slate with Wifi AND Data (Verizon/Sprint) to use for navigation, communication with family, and management of your banking.
On this tablet, I would have my Amazon Kindle account. I already have a library of 1500 free and paid books.
2) I would convert as much as possible to lightweight multifunction clothing -- camper pants that unzip to become shorts. Take all necessary linens, towels, etc.. but plan on frequent regular stops to wash clothes.
3)Food is easy and can be purchased at WalMart while you overnight in the parking lot.
4)If I planned to boondock, I would bring my generator. I also have a locking cable to secure the generator a bit, should it desire to take a walk in the night.
5) I would make sure I had a good basic set of tools, get as many multifunction tools, include a good digital multimeter. I use a power drill for my jacks, so I would include a set of bits to fit this drill. Include a tire inflation pump and tire patch canister. Make sure you have a lug wrench to fit your trailer lug nuts. I know the jack crank fits them, but I bought an 18" breaker bar with the correct socket.
5) Trim down the galley. Use collapsible bowls, kettles, coffee makers when possible. You know your cooking style, but forget specialty things like a waffle maker. A pancake tastes just as good and can be done in the same skillet used for scrambling eggs or frying bacon. I would include a hotplate. We never cook in our pod, except for that first cup of coffee on a brisk or rainy day.
6)Get a good first aid kit, make sure you have the basics covered - perhaps take a Red Cross first aid course. Remember the order: Bleeding, Breathing, Poisoning...
7) Talk to your doc about any needed prescriptions and how to manage medical needs, including insurance, on the road.
8) Connect your tablet to a cloud. I use Microsoft Sky Drive, it is free to start and super cheap to expand. I do not store any important or sensitive information on my tablet. It is all on my SkyDrive. I store all passwords there, but have coding system. For Example if my password is Hippopotamus1234 I record it as Animal1234. Only I know that Animal is Hippo...
If you lose your tablet, they get nothing. You can go to any public library and downlosd these lists from your skydrive. Make sure you include all your contacts, family addresses etc. on the Skydrive. I also put all photos on the Skydrive.... I had a laptop stolen years ago and lost valuable digital photos. Never again.
9)Depending on where you plan to go, I would probably pack my Glock. Just don't go to New York. I don't want to become a victim changing a tire on a lonely road.
10) I have two batteries on my pod. I also carry three flashlights with LED bulbs.
11) Get some kind of campground polarity electrical pole polarity checker. Mine has some led lights that show a pattern with the correct voltage and grounding is in place. I have the service cord for the pod and I carry an extension 30A cord.
12) For a trip like this, please do some sort of Journal. We did the Lewis and Clark trail and still have that journal. While driving the trail, we listened to the Audio Book Version of Undaunted Courage by Stephen Ambrose -- it is a narrative of the Lewis and Clark journal.
13) Of course you will have your telephone, but get Skype on your tablet, learn to use it, and teach your relatives how to use it. Even if phone goes out, if you have WiFi you can call anyone.
14) Bring a bucket (and a bucket list

) can be used for emergency dumping when you cannot move the pod.