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Good Tibetan Guides are useful, I like to use someone the local hotel recommends. I stay at the Snowlands Hotel, in my opinion it is the best family hotel. Jeep tours are a popular way of getting around Tibet, while not cheap, the tour operator will sort out all the necessary paperwork, and they offer you a reasonable chance of sticking to a schedule.
Your driver will likely be an indiginous Tibetan who can speak Chinese. He'll get to eat and sleep for free wherever you go (he'll often be treated like a king), and he'll often need to stop for a smoke or a pee by certain vendors on the road. 4500 RMB will get a jeep that can seat 4 people and luggage comfortably for 4 or 5 days.
Be very precise with your itinerary and very careful with payment. Every stop, monastery and lake you wish to visit, etc should be written on the itinerary. Payment should never be made in advance. Many foreigners, especially pro-Tibetan ones, are so trusting of Tibetan drivers that they hand over their money in advance but never get to see their drivers again.All that bad stuff said, if you find him yourself and pay him a decent wage, talk about what exactly you want you build a rapport easily. If you want to find goodies, tell him if there is noone to translate, tell him through hand gesture. If he does really good, you can give him a tip. Or hold back, give him what the travel agencies give- 4-5 days he will get 2000 yuan, including gas. Tell him 1250 in front, 1250 back and if he finds some goodies cheap 1250. Tell him not to make his own deals if he is working for you. Watch to make sure he isn't double dipping from the seller too.