Awesome, thanks for the wonderful replies. I'm just going to dump all my responses in this post, instead of shitting up the thread with 9 add'l posts.

/u/211logos - November. Now that I think about, north I won't be able to camp, but getting down into Nevada/Cali should be alright. Thanks for the recommendation - I'm going to take a look and figure out what's along my route.

/u/OchoC / /u/cirena - my plan is going West up to Swift Current (Canada), then go down through central Montana, eastern Idaho, down to SLC, take the 6 to the 50 all the way to Reno.

From Reno, I think I'll take the suggestion of the 395, bypass L.A to the North and get to Ojai so I can still hit both the 395 and the 33.

It's getting back that I'm running into a snag - I'd like to take the 1, bypass Big Sur, and then hop back on the 1 to do the Coast Hwy drive, but I'm not sure if I'll have the time? Doing the math I can get to Cali in 3.5 to 4 days of driving (I'm used to 14+ hour long drives), maybe even less, leaving me about 5-6 days to hang out and sightsee.

Getting back I'll have roughly 5-6 days, so if anybody has any insight on the Coast Hwy plan I have, I'd love to hear it.

/u/kyle415 - thanks for the recommendation! It looks like it's on my route from the 1, if I just keep going to the 101. Let me know what you think.

Again, thanks for all the help everybody. This is kind of a fly-by-the-seat-of-the-pants trip for me - I love to drive, I love to plan random trips, and I've always wanted to visit the desert. I know some of you might be thinking "this guy's nuts and will never get this done", but.. determination is a powerful thing.