Replying to Cross country road trip

In a few weeks, my girlfriend and I'll be embarking on a six week road trip across North America, and I'm hungry for some tips for surviving that much time living out of a car. I've done plenty of weekend car camping trips and slightly longer backpacking trips, but nothing quite like this. Since the road trip is also part of a big move, there's going to be a lot of stuff we need to bring, too. I trust the collective experience of Newschoolers to offer some friendly advice.

The route: From Hartford, CT to Mammoth, CA, by way of Denver, Jackson, Bozeman, Lake Louise, Vancouver and down the Left Coast.

The vehicle: A 2013 Subaru Outback - the perfect car for long journeys into the mountains.

The gear: 3 pairs of skis, 2 mountain bikes, 2 skateboards, climbing equipment, 2 three-season tents, 2 hammocks, normal camp cooking supplies, and everything else we'll need for a winter of SHREDDING in Mammoth.

The organization: We currently have a large roof box for the skis, poles, and some other gear, and are trying to figure out the bike rack situation. If we can fit two roof racks next to the box we can have easy access to the trunk, but we may end up needing a hitch mounted bike rack. I'm tentatively planning on storing extra clothes, winter gear, and things I don't need for the drive but will need in Mammoth inside those big plastic tubs. For things used frequently on the drive (cooking supplies, sleeping gear, toys), I'm thinking of using those shitty plastic drawers everyone buys before going to college and placing them all the way to the back for access through the trunk.

The Questions: What should I know / do / bring that will make this experience be an enjoyable one and not a month and a half of disorganized hell? I'm especially curious about optimizing the arrangement of storage in the car so I don't have to go digging every time I need something. Where do you put the bulky things like ski boots and helmets? Is there a way to keep food refrigerated for more than a few hours? What is that really important thing that I haven't even considered because its so obscure but makes everything better?

Thanks!