As of today I only have 28 days 'n a wake up to go before my Exodus begins. I've been selling all of my stuff and also putting together a running list of things I will want/need to bring with me and I was hoping to get input from y'all as to what else I might add to the list based on my plans.
So, I'm starting this thread and will update it as D-Day (September 30th) gets closer.
My general plan is this -- on September 30th I'm beginning my journey from the upper midwest to La Frontera, or the Mexican border for you gringos on here.

Once i arrive at the border city of my choosing, I'm going to put my car into storage for a few months pre-paid. Then I'm going to strap on my backpack, take a bus to the border, and literally walk across the border on foot. From there I'll take a bus to whatever city in Mexico I plan to check out and stay in first. After a few weeks in Mexico, I will secure a Brazilian visa at a consulate in Mexico, and then head to South America. I MIGHT also head to SEA for a couple months of backpacking (Want to check out Vietnam, and yeah, will have to check out the Philippines so I can finally see what all the hype is about!) but depends on a lot of things, like how obsessed I get with Mexico/Brazil, have I met a girl to share my life with yet, do I want to start working sooner or later, etc etc.
I don't plan on spending time sleeping outdoors but am bringing a full range of supplies just in case I get caught without a place to crash for the night (tent, sleeping bag, etc). Also want to carry an emergency supply of food and water with me that will last for at least several days. So, here is the list I have built so far. If you think I should add something to it, let me know!
Passport
Birth Certificate
Divorce Paperwork
car registration renewed
Laptop
Ipod/music player
Headphones/earbuds
Deuter Traveller 70+10 backpack
tent
sleeping bag
pillow
ibuprofen
stomach medicine
first aid kit
swiss army knife
hatchet or machete (maybe better to buy in-country?)
food for at least 3 days of emergency rations
- canned chili for lunch and dinner?
- something small and portable for breakfast
water
canteen or other water carrier
flashlight
large lighter
locks for every zipper/compartment of backpack
bike lock for securing backpack to objects as needed
bug spray
sort any music, videos, and software that you want to bring on laptop/ipod/etc
I am planning on opening a Citibank account to use for ease of access to funds abroad. Will probably keep my current bank account and leave a few grand in there as a backup/safety net however.
I plan to avoid ATM's like the plague, especially in Brazil. I would prefer to do all my withdrawls abroad in actual bank branches for security and safety.
By the way, anyone have any good recommendations for a cheap new laptop? I don't know how good and user-friendly Windows 8.1 is compared to 7, but you can't get new 7 laptops any longer it appears. Essentially I need the laptop for SECURE online banking while abroad, playing the occasional movie and plenty of music, working on a website for possible online income (SEO Writing, English teaching, etc), decent face-to-face communication capabilities via webcam (for teaching as mentioned, plus making new contacts with people etc.). Not too worried about gaming or anything like that. Gaming will be the last thing on my mind, after all, I'm going to be living as close to a real-life RPG as you can get!

Really looking forward to your input guys. Getting down to the wire now!