Are pictures necessary? A tool list might be all that's needed.

For Santa Rosa Island my immediate thoughts would be:

• Communications -- If cell service isn't reliable I would consider a satphone, PLB, or perhaps a ham radio as being essential. The PLB would be my "default" choice. I would really like to have a communications plan that involved regular check-ins with a reliable person.
• First Aid -- Covering boo-boos (with a focus on footcare) and traumatic injury.
• Tools -- A full-size multitool, bit kit for same, duct tape, along with any tools needed for the purpose of the expedition.
• Appropriate clothing and footwear, with clean socks to wear every day
• Food, stove and fuel (assuming that the no fires rule doesn't apply to stoves)
• A whole lot of water
• Tent, mat, sleeping bag
• Flashlights and batteries
• Something to read before bedtime

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I never forget my teddy bear, and neither should you!

At the moment, I'm not going anywhere and don't have any plans to do so in the immediate future. I have seen other people do somewhat long term volunteer/ missionary trips although I never got the full details of their trip. Factors like climate would certainly play a role but I was curious about some of the basics on such a trip.

I would think it imperative to understand the customs and social situations where you will be spending time. There are places where it is a grave insult to show the bare soles of your feet, for instance; or to point with your finger.....

Trying to hitch a ride with your thumb in Russia, Mideast, or North Africa will probably get you run over. Like "V" for victory or peace, with your palm in, while in most english speaking countries, it's the regional equivalent to the bird.

Handling anything communal with your left hand in the Mideast or Asia Minor is a good way not to get invited back. Ever. Your left hand was, historically, for cleaning your rear.

Yeah, that's a way too wide question. My first thought after reading news all day was: is he going to join ISIS? Seriously, typical volunteers are usually invited by those countries in need somehow and definitely not for just surviving off the land somewhere in a desolated desert with no people around. Almost certainly some survivable living conditions will be provided for them. So I would concentrate on:

1. Personal entertainment. For me that would be a decent tablet with plethora of software, games, ebooks, manuals, music, video, learning courses, podcasts collection, family photographs... But usually Internet is also available at least at some spots around, even deep in the Africa. But, perhaps, you might consider investing in a long range directed WiFi link extender. Make sure you know how to install it, and take it with you (there are models you don't have to hook to the base camp router, just arrange its powering with the owner of the base hotspot). Don't forget about the solar charger (7-40W) and a battery powerbank. Though, most likely you will have a normal power outlet in your shelter, - the power may not be readily available when you need it (e.g. in N.Korea the light is centrally turned off at night for energy conservation).

2. Personal health. I'd take all possible immunizations viable for the region beforehand. The SteriPen for water sterilization (entertainment charging solutions above will make it work indefinitely, just make sure you have at least 2 spare sets of rechargeable batteries for it) - mandatory in equatorial countries like India. Assemble a serious enough emergency FAK with trauma kit and chronic meds you need. Stock on multivitamins for the period. Get most durable outer clothes and footwear you can afford for the expected climate.

3. Making friends. Make your "entertainment kit" suitable for enjoyment by a small party (multiple game controllers, amplified audio, maybe stereo glasses or/and small DLP projector). Load it with information about the country you are visiting, including foreign language aids, some books, music, and movies in local languages if possible. Perhaps, you can master some locally popular board, table, or field game. Depending on the age of your gonna be friends, I'd bring a bunch of small but useful or entertaining gifts to give out. Tiny MP3 players with earphones, small multi tools, keychain flashlights, fishing lures, pocket games - what comes to mind. Perhaps, collectors items like post stamps, postcards, coins... If not directly for your friends - then for their children. Avoid USA symbolics on your gifts though, in many developing countries that might cause troubles if not for your then for your new friends (however, in some countries that could surely have a totally opposite effect to your benefit).

At any rate, learn the region's culture and needs. Perhaps, you could master a sustainable skill or two which are in high demand there, so you can trade it for some local amenities or obtain personal preferencies. Take with you all the necessary tools to efficiently practice them for locals.

I must vouch for Russia - hitchhiker's thumb-up is well known and respected there. Even though its original meaning is closer to "OK"/"Great"

Not just historically. There are still lots of places on this planet where toilet paper is a scarce commodity. So you'd better bring your own personal supply unless you're completely comfortable with the old school alternative...