If you have the internet with you (or some other reliable means of accessing it on the road), I can see things being a little easier. Check out WWOOFing, maybe, and definitely CouchSurfing. If you're sending out CouchSurfing emails every day as you go, you should be able to find plenty of free places to stay and probably a lot of food and other charity as well.

But what the others said about the American West is absolutely true. It can be desolate.