Your idea is very good. The west coast is an easy place to hitch/ travel, since it is warm outside and there are many people living this life. Some options: if you want to stay in one place (for example SF) for awhile, you can often find temporary work at a hostel, like cleaning rooms in the morning in exchange for sleeping there.
Try to be smart about drugs/ alcohol, when you are traveling, sleeping outside, you have to be more responsible for yourself.
Another place to know about is Slab City in southern California, it is a hobo camp in the desert with a pretty good diy skatepark. It is a very crazy place unlike anywhere else, can be kind of scary, but you can live there for free as long as you want and you will meet some of the most far out people with incredible stories. Good luck and enjoy, I hope you do it.