Possible, but make sure he has it registered planned non-op. otherwise, unlike some states, the buyer is responsible for the fees and late charges. Which are incredibly ridiculous. If you want to be sure, just go to any highway patrol office and ask them for a list of things a car must have to be street legal. they will give you the law in writing.
And if you so desire, you can take the truck there and they will do a walk around.
Otherwise the answer to your question is YES...Will it be a pain, PROBABLY. Worth it, MAYBE depending on the cost. Put in the research to be sure for yourself. It has to pass inspection and it has to pass smog. All the other stuff you can choose to take your chances, but people are getting hit more frequently for small violations.
Here is the thing, rock crawling capability is inversely proportional to streetablity. The more you build that truck to crawl, the less "friendly" it is on the road. If you are new to the game then my suggestion is buy a different truck. Buy a pickup/tacoma/4runner that is more stock. It will be cheaper. Wheel it mostly stock for a while and DD. As the years go by build it to your liking. Just like anything else, throwing more money and parts at a project may not get it up the hill better and it especially wont make you a better driver. If you are in CA 31's-33's on open axles can get you up 90%+ of trails just fine. those 39's are for the top .5% of trails. In fact, I've seen a jeep up sledge hammer, claw hammer and the wrecking ball on 33's..sure he had a winch for a few sections, but he did good with minimal damage...This particular person is well known and an excellent driver. Choosing lines and learning techniques is "free" and worth much more than just building something or buying something with the best parts and expecting it to get itself to the top.
Just my 2 cents...I would suggest something post 22r's like any tacoma. I think you may be happier with the motor options of late 90's+
Just my 2 cents
