As someone who has spent a decent amount of time in that area, I would suggest flying out, catching a ride to your friends place, and just buying whatever looks cool on the side of the road instead of this "preparing" thing.
I would also suggest heading an hour or so north to Santa Rosa, and setting at Russian River Brewing for a pint of Pliny the Elder.
Why no sports cars?
Alfa, Fiat, MG, Supra, 280XZ, etc?
Some of those I've not seen for decades, and are still cool. Maybe even a RWD Celica.
https://sfbay.craigslist.org/nby/cto/d/1985-porsche-944/6666791260.html
or in shape ready to do the trip with nothing...
https://sfbay.craigslist.org/eby/cto/d/porsche-944sl-16v/6657759133.html
Mine has turned into my, by far, favorite distance-cruising car I've ever owned. Actually my favorite car to drive, period. The only kinda problem area is timing/balance shaft belts not being done, and the second one had them done this year so would be ready to do cross-country, IMO. I plan to take mine cross-country one day when I have time. Buy-in is similar to other things you're looking at, and there is always a market for them out east in good shape. But you may actually want to keep it...... And they don't rust. And you'll get near 30mpg
a couple of things , California has never had yearly safety checks......
and if you start in the Bay Area and head east its less than 250 miles going over the 7000 ft Donner pass to Reno ,
If it makes it that far it will probably make it anywhere !
PS......have Auto Club plus to save you if needed :)
Does a Autumn trip mean no AC needed, so, Air Cooled?
The problem with VWs and Porsches is I question my ability to locate parts if something goes wrong. The other sports cars seem hard to find in a cheap enough price range, but I'm all for it if you guys are finding them.
i'm feeling that torino wagon on aluminum slots with a white stripe down the side and up the C pillar, like for when Starsky and Hutch got married and adopted some kids. but it's a super base model, no AC.
That Galaxie needs more chain steering wheel!
Local guy selling a four car trailer for $2500. Buy a one ton diesel, four car trailer, load the trailer as you cross the country and sell all but one when you get back. 
The extra cash will help in your search for a new place to live too.
I'd go with the Mighty Max, but I might be a bit biased.
I'd expect parts for an air cooled VW or older Detroit iron to be some of the easiest things to find in a emergency. My vote is for the low-rider or the Bug.
my vote is an old late 60s, early 70s American pick up or van ,
simple mechanics if they need to be fixed
I vote for a smaller wagon, then drive it down to hit the challenge before going back up north. Bonus points if you summit pikes peak along the way.
In reply to bluej :
Already have challenge plans this year! https://grassrootsmotorsports.com/forum/grm/2018-challenge-parking-lot-build-aw11-mr2-supercharged/142277/page1/
¯\_(ツ)_/¯ said:The problem with VWs and Porsches is I question my ability to locate parts if something goes wrong. The other sports cars seem hard to find in a cheap enough price range, but I'm all for it if you guys are finding them.
In this day and age, worst case you get on your phone, get whatever you need via Amazon, and get a hotel room and it'll be there the next day lol.....
I think one good key for whatever car you end up getting is to spend some time finding a few people in strategic areas around the country who have parts stashes or parts cars. For example, i know of at least four people who part out 944s and have several of them sitting around. I can literally probably find someone with any e30 part within a hundred or two hundred miles of most areas of the country.
The one thing about the Porsches (not necessarily VWs) is that they're galvanized, so they don't rust away in junkyards and probably stay on lots longer than many other cars, until stripped. And there's always a busted one on CL wherever you may go that someone gave up on and just wants to sell for a few hundred bucks lol. There are a lot of VW and Porsche facebook groups, to boot.
But with them, there are a few known things (like carry a spare relay for the DME - which I have like 4 of), but not any more "unusual problems" than any other car, really. Most of the 924/944's problems are dumb things like window motors, leaky sunroof, hatch glass separation, rusting battery tray (the only place they do rust), and wonky gauges. This week one of the TWO radiator fan relays went bad ($70 from Porsche), which can't be bought at any auto parts store. But you can still bust out some primary wire and a general-use relay and jump it like I did....no biggie.
Not much to go wrong with the suspension, and engine is solid if the belts have been done recently. I mean, if you blow the engine or trans on pretty much any non-normal car, it's gonna be an issue on your trip, so not much different here.
if you're ok with a little higher buy-in, this reeeks of everything 80's awesome:
or bring this back for $1800 and sell it to me:
Classic American iron from CA is a bit of a gold mine. No rust (although some SF salt air may have crept in), and selling it anywhere else is easy.
There are also some cheap gems out there. I picked up a 62 Caddy SDV for $1500 that ran and would have made the trip as long as you had a case of oil with you. I had a 73 Impala station wagon with 58,000 miles and a 454 that I got for cheap and made a fair chunk of profit when I sold it in NY.
btw, while pipe-dreaming about my own XC trip, I ran across this article. non-S 924s are out there, and dirt cheap. And apparently very reliable.
https://www.pca.org/news/2017-05-30/two-thousand-miles-2000-porsche
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