Supplies!

Having been a boyscout, I'm very familiar with the motto: "be prepared."  For such a long trip in such varied locations and the climates that come with those locations, it is necessary to have quite an inventory of items.  Also, not wanting to forego all comforts, there are additional items which aren't necessary, but definitely convenient.  Planning to cross into Mexico and Canada also places some limits on the things I can conveniently bring.  This is obviously a lot of gear, and for the sake of fitting it all into my vehicle, I referenced a number of sources in choosing some of it, many of which were geared toward backpacking.  While not all of my gear is the smallest and lightest, I tried to balance the concerns of budget, size, weight, and durability.

Gear:

To Camp:
Tent: Big Agnes Slide Mountain 2 with footprint (not the lightest or most compact tent out there, but very good quality, and it was on closeout for about 75% off).
Tent Stakes: MSR Groundhog stakes - while the tent comes with premium quality stakes, these are some of the best available.  Given the amount of use this tent will be getting, it was reasonable to pick up a set of better stakes for tough ground.
Sleeping Bag: I have an old coleman bag that is suitable for about 40*, but I will be in some areas that can get quite a bit lower than that.  I found a Sierra Designs Pyro 15 down bag on closeout for about 50% off, which should keep me warm, and compresses nicely for any backpacking excursions.
Mattress: Nemo Cosmo air mattress with pillow top for comfort, and a Therm-a-Rest Z-lite for when I don't want to take the time to inflate the air mattress.
Pillow: Therm-a-Rest medium compressible pillow.
Chair: GCI folding chair - folds small and flat.  It's not a necessary item, but certainly nice to have a good chair with you.
Table: RIO expandable table - roll top aluminum table, suitable for cooking on and eating off of, or even charting a course on a map.  Like the chair, it's a luxury item, and many established car campsites will have some sort of table, but it's nice to have for those times you don't want to rest your plate on your legs while you eat dinner.

To Hike:
Day/Hydration pack: Osprey Manta 30 - about the size of an average backpack, and it included a hydration bladder.  Really satisfied with it in my initial testing for a day trek around Weedon Island.
Weekend/Trek pack: Osprey Aether 60 - one of the few packs that actually fit me well when I tried them on at Bill Jackson's.  It's also fully compatible with the hydration bladder from the Manta pack, so I don't need to go without easy access to water when I'm hiking further.
Trekking poles: Leki Corklite Speedlock poles.  These may seem like a silly thing to a lot of people, but these are useful for hiking off the beaten path, or even on a beaten path when you've got a pack strapped to your back.  Conveniently, both packs have stowage loops built into them.  I also have the snow baskets, so they can be useful whatever climate I encounter.

To Survive:
First Aid: Adventure Survival Kits SOL Hybrid 3
Paracord: general purpose helpful stuff to have around - 100 ft orange, black, and olive (all military grade 550lb and 100 ft military grade 100lb
Carabiners: Though I had some basic utility caribeeners sitting around, I got a couple of Black Diamond Oz carabiners that are rated for climbing.  They are overkill for just about any of my purposes, but can easily support my weight if I need to use them and the paracord for some sort of emergency purpose.
Matches: Water tight container of 25 waterproof matches, 2 boxes of 300 cooking matches.
Flint: Gerber Bear Grylls "flint" and steel - not that I think he's necessarily the best survivalist out there, but this seems like a good product, as are many of the things Gerber makes (not the same company that makes baby food).
Flares: 2 military grade 12hr Green Cyalume Chemlights
Shovel: U-Dig-It folding stainless steel shovel (had I seen the one at a local Walmart first, I'd probably have gotten it instead, but this one wasn't much more, and is better quality). Useful for...digging...for...you know. Also, just a good tool to have with you.
Axe: Cold Steel Pipe Hawk (not a functional pipe hawk, the "bowl" end is solid, making it a useful hammer, but having the style of a traditional pipe hawk.
Saw: ARS 210DX folding pruning saw.  A little bigger than the average pocket size, but it will conveniently fit in any pack.
Water Purification: Sawyer PointOne Squeeze water filter system, Katadyn Micropur tablets.

To Navigate:
Maps: I raided my local AAA office, and took just about every map they had!
GPS: TomTom XL 340S (found this on clearance before I left my old job - my mom bought it for about $45. Borrowing it from her for the trip).
Compass: In addition to the button compass in the SOL kit, I have a Suunto M-3 that was a Christmas present from my brother.

To See:
Lantern: Black Diamond Apollo lantern
Headlight: Petzl Tikka2 that was a Christmas present from my brother.
Flashlight: I always keep a 3D cell bronze colored (black can be hard to find in the dark) Maglite in my car for miscellaneous light needs, and have several others in various sizes.

To Eat:
Stove: MSR Whisperlite International - the quintessential liquid gas stove.  Also have the 11 and 20 oz canisters for this, and the full maintenance kit.
Stove: Coleman classic camp stove - propane based stove.
Pots/Pans: MSR Alpine 2 cookset, Lodge cast iron 10" skillet/fryer combo
Dishware: GSI Infinity 1 person set.
Flatware: Snow Peak Titanium Spork - probably my single favorite piece of gear! This is upplemented by a GSI glacier stainless 3 pc flatware set.
Knives: Farberware Resin knives (chef, santoku, pearing, and utility), each of which come with their own plastic sheath.
Utensils: GSI Crossover Cookset, GSI stainless mini Whisk, MSR Strainer/Grater
Storage: Aside from the obvious Ziplock bags, a set of Rubbermade storage containers.
Trash: Sea to Summit Big River 20L dry bag - can be hung to keep rodents out, if needed.
Kitchen Sink: Kelty Kitchen Sink - doubles as a storage compartment for most of the cookware, or can use as a cooler, because it's water tight.
Cooler - Igloo 38L 5 day cooler.
Water carrying: Kleen Kanteen 16oz double insulated stainless steel water bottle with Cafe (sip) lid and stainless loop lid, MSR 6L Dromedary bag.
Soap: Campsuds soap - picked this up cheap, and though it seems to do a decent job, and is mild enough to use for hair/skin, I would probably just buy a small container of concentrated dish soap to replace it if it runs out.
Canopener: Military P38.
Cookbook: The Scout's Outdoor Cookbook - always nice to have a reference when cooking.  This one is geared more to groups than solitary travelers, but it seems to have some good recipes.

To Not Stink:
Towel: Sea to Summit Drylite XL towel - it's actually larger and softer than your average bath towel, MSR Packtowel Ultralight medium towel - odd dimensioned rectangular towel, useful as a sweat rag, or for hiking trips.
Soap: Coghlan's soap caddy (I like bar soap, and this one can be hung around the neck, a branch, or whatever I find to keep my soap high and dry).

For Storage:
Drybags: Sea to Summit 14L and 30L eVent Compression Sacks - though the sleeping bag I have came with a stuff sack, it's not a compression sack, and with the 14L, I can compress it to about the size of a football.
Nylon mesh bags: Set of 3 nylon mesh bags - bought to have a bag for the bath towel (it's the only one I've seen that doesn't come with it's own bag), and the other two are suitable for separating socks and underwear, or whatever I come up with.
Toiletries/Shower bag: Samsonite boarding bag.
Hamper: 2 Coghlan's canvas laundry bags.

For the Car:
Power Inverter: Tripp Lite PV375 375W power inverter - capable of charging my laptop, cell phone, and Dewalt batteries.
Vacuum: Dewalt battery powered wet/dry vac
Shovel: Lifeline snow shovel - it's cheap, it's sturdy aluminum, and it's small.  I might not need to use it, but it's worth having, just in case.
Ice Scraper: Hopkins Ice Hammer Snowbrush
Chains: SCC Super Z6 chains (1pr). You don't often see somebody in Florida testing snow chains on their car, but it happened.  Even through April and May, there are some states that mandate snow chains, and quite frankly, if they're mandating them be carried, I just might have to use them.

For the Bears:
Bear Canister: Bear Vault BV500 - it is no longer legal to hang a bear bag almost anywhere, and mandatory to have a bear canister.  They are available for rent in many national parks, but if you're going to be in bear country for a while, you may as well have your own.
Bear Spray: Counter Assault 8.1oz with holster.  Though this isn't always effective, it is one of the few protection items that are feasible to take into Canada.

Clothing:

Footwear:
Shoes: The North Face Hedgehog GTX III - these are waterproof, Vibram soled trail runners that are comfortable for casual walking, while being well suited to light trails.
Boots: LL Bean Cresta Hikers - these are full on all leather hiking boots, suited to just about any terrain.  They also have a Gore-Tex liner, and a Vibram sole.
Sandals: Teva Deacon - water friendly sandal that can be worn anywhere, including showers and light hikes.

Headwear:
Sun/Rain Hat: Tilley TWC4 Outback Hat - for sun and water protection of my dome.
Wool Hat: Bethleham Trading Post hand knit wool monmouth cap - to keep my dome warm.
Baseball Hat(s): Rays, Lightning, and/or Bucs Hat for general use when I want a more typical hat.

Raingear:
Jacket: LL Bean Stowaway Goretex Jacket
Paints: LL Bean Trail Model Rain Pants
Belt: Bison Designs (LL Bean branded) - Strange as it may seem to list a belt as rainwear, I usually wear a leather belt, which is not ideal for wet environments.  For this, I have a woven nylon belt.
Waterproofing: Nikwax GloveProof, Cream Wax, Fabric & Leather Proof/Footwear Cleaning Gel Combo pack

Other:
Obviously, an assortment of warm/cold layerable clothing is in order.  I could list much of this, but instead, I will just state that most of this is sourced from Columbia, Under Armour, and LL Bean.