Not sure what kind of hotels you'll find out there, but $35 is pretty optimistic. You can pay that for a tent site at a campground with showers. There are deals to be found of course, but I seen some pretty major dumps getting $80 and up and then there is usually at least 10% or more in taxes. (I've done four multiday trips this year sleeping outside. I hate sleeping outside. But hotels were $120 and up a night. I slept outside and used the savings to buy food in restaurants.)
If the weather sucks (including wind, rain, heat, cold) it will be all the more important that you take occasional refuge in a restaurant (especially if you are sleeping outside.) Starbucks has excellent bathrooms (and air conditioning and electricity) you can use for the cost of $1.50 cup of coffee.
If you go with polypropylene underwear and t-shirts, you can get by with two or three sets total. In the desert, I shower in/alongside them, and, in the summer, just wring 'em and wear 'em. (They dry in minutes if it's hot.) When I went to Death Valley I was able to get by with ONE set of boxer briefs/tshirt - and they were clean every day. Ex Officio is a top of the line brand for this sort of thing but you can get them for cheaper.
If I had to cut down on my stuff, I'd get rid of the food (and means to prepare it) and eat as needed along the way. Keep a couple of Power bars for emergency. If you sleep outside, you are going to need a sleeping pad of some sort at a minimum and, a tent, unless you like bugs and rain. If it's warm, you don't need a sleeping bag, but it's hard to predict and most places don't stay warm all night (except maybe Joshua Tree and Death Valley in the summer.) Ask around - odds are someone you know has a Thermarest that they'll loan you. If you are strapped for cash, just buy a cheap tent and throw it away it if doesn't last. You can get a Walmart tent for under $100 and I think it will pay for itself if you use it twice. Sort of. Many people have tents they aren't using in their garage - the key is - you need small and light. I have a REI Half Dome 2 Plus - it's a pretty good tent but I think it's like $299.
I carry a couple of knives and a small axe when Im on the road. Besides the practical use (like hammering tent stakes), it's nice to have something lethal handy when a pack of coyotes starts sniffing at your tent (yes) and, to a lesser extent, vermin of the two legged variety.
Alazar, I've got a ton of books onthe subject I'd be happy to lend you and I'm not far from where you live. We might even meet up at the top of Palomar for a "dry run" (Doane's Family Campground) I highly recommend a couple of shakeout trips. Do a three day trip like this. Night one: Outdoors at about the distance you plan to travel. Night two: Back home, regroup, re-pack. Night three, somewhere different that Night one at about the distance you plan to travel. Night four: back home. This will give you minimum risk and maximum learning curve. You might shoot for Joshua Tree for one of the nights.
Stay flexible and try to focus on the "adventure" aspect. Shit will go wrong, but as long as it doesn't kill you, it will make the experience that much richer.
