A crucial piece of any expedition is getting there, and how you get there frequently dictates what you bring and the manner in which you pack it. There are many options, each with their own caveats. It's not usually the getting there that is problematic, it's the getter there there with all your gear that can create issues.
Planes are great for long distances, but you'll need a car when you get there and you have to catch the deals. Plus, you need to fly Southwest unless you like getting reamed by checked bag charges. If you do fly, absolutely weigh each bag before hand to make sure they come in under the weight limit. Also, avoid multi-stop flights to minimize the chance of losing your bags. Don't even think about trying to fly with a stove, fuel, crampons, or ice axe. (Well, think about it long and hard in order to figure out the best way for you, but it probably won't be easy or convenient.) You can always try shipping things ahead of time to the post office care of general delivery. If you're talking about a bush plane, well, you're way out of my league...
If you've been paying attention, though, you'll note that Susan and I are going on a roadtrip, which leads to my preferred means of transportation--the car. I like to think of my car as my mobile home base, and it's important to get "the rig" properly equipped for the anticipated travel.
For the actual driving itself, consider where you're headed. Do you need four wheel drive? High ground clearance? Mud tires? Snow chains? Studded tires? Bear in mind that if you're traveling long distances that all of these things reduce fuel economy. Plan accordingly.
Ideally, you also want to be sure that the vehicle is in the best shape possible prior to departure. I like to have an oil change and inspection, relatively fresh, properly inflated, rotated tires, good windshield wiper blades, and a coat of rain-x applied to the glass. Also, bring along a set of jumper cables and an ice scraper at a minimum.
When living out of the car, the two most effective ways to make life easier are 1) electricity and 2) organization. If you don't have an A/C outlet in your car (our Toyota Matrix does), a power inverter is a must. Bring chargers for the laptop, cell phones, and any other electronics on which you will be depending. I like to stash all of these as well as some spare batteries in the same location in the car so I always know where to look when something dies. That being said, don't make the mistake of leaving something plugged in when the car is off. Similarly, turn off the dome lights or be ready to close the car doors every time you get in or out. It's not usually a problem if your headlamp dies, but it's definitely an issue if your car battery goes. You did bring the jumper cables, didn't you?
Staying organized while living out of a car definitely takes work, but it makes life infinitely easier. I find a selection of Rubbermaid tubs and bins to be indispensable. The under-the-bed size ones work well in the trunk or rear with the seats folded down and can make a nice flat surface for tossing other stuff onto for sorting, re-organizing, etc. They are also great if you plan on building a custom bed platform for the back of your ride. A few durable duffel bags and even a reusable grocery bag or two usually do a good job of taking up the space in the floor between the front and rear seats. Anything that will be needed frequently or while driving should live up front or just behind the center console. Things that usually end up there when I'm living on the road include a road atlas and other maps, change for road tolls, a headlamp or two, phone chargers, toothbrush, prescriptions, a pack of gum, duct tape, and a pen.
The ultimate rig allows you the option to sleep (relatively) comfortably. If there's still a steering wheel in front of me when I'm dozing off, I don't usually consider that to be comfort. Luckily, there are various decent systems for sleeping in the back of many vehicles.
The classic roadtrip vehicle is already equipped for the job--think a VW Westfalia, or perhaps a Dodge conversion van. Even if you aren't driving a vehicle with dedicated space, if you drive a Jeep, SUV, hatchback, or even large sedan, you can probably rig a decent sleep system. The basic idea is the same--fold the rear seats down and move the front seats forward until you have enough room to lie down. Fill in any gaps and make things as comfortable as possible.
In our Matrix, the rear seats fold down nicely to be level with the trunk space, giving a large flat platform to work with. Pushing the front seats all the way forward gives ample room to lie down. Stuffing gear in the floor space between the front and rear seats continues the level platform and avoids sagging into what would otherwise be a gap in the sleeping surface. The whole thing gets covered with a few sleeping pads and sleeping bags. Finally, any other gear gets shoved up front. The conversion process from "drive mode" to "sleep mode" only takes a few minutes, provided you don't have too much stuff to move around.
When I'm traveling solo, I just leave the gear on the driver's side of the car and sleep on the passenger side, requiring no conversion time. This system can also be used if you need to get somewhere in a hurry. The passenger can nap comfortably and switch with the driver every couple hours.
Sleeping in the car means you can often leave the tent behind when you would otherwise be car camping, saving tent set-up and providing a comfortable, equally warm, and possibly drier shelter. If you'll be sleeping in the car in more public areas, it can be nice to have a little more privacy.
This can be reasonably accomplished with well-tinted windows and a sunscreen for the windshield, though prying eyes can still see inside with a little effort. Another option that I have employed in the past is to run some cord between the "oh shit" handles above the passenger seats. Then, simply draping a towel, blanket, or clothing over the line creates a privacy shade. A friend of mine has equipped his rig with a piece of velcro glued above and below each window that has a matching piece of cloth cut to size. This system also works well.
The other important detail to take into account is ventilation. This easily overlooked point is made painfully obvious on a humid summer night or a sub-freezing winter morning. (It's exciting to wake up and discover your windows are iced over on both the outside and the inside). Window vent shades allow you to crack the windows while still protecting the interior from rain and providing enough ventilation to prevent condensation build-up.
With only a few small adjustments and a little time and effort, a car can be easily transformed into a road-ready rig. For those willing to expend additional time and money, sleeping platforms, storage spaces, solar showers, and integrated mini-kitchens are just the beginning. The limit is simply your creativity.