2nd Gen Tacoma buying help

Well I guess I will go out on a limb and be the first to answer the man's question... For that price range the years you will most likely have access to would be 05-09. Being as how he is 16 I would imagine that he will be driving the truck for at least 4 years before a different one is purchased. That being said I would probably look at mileage less than 120k. These trucks don't really have a ton of issues, and the majority of maintenance items would be taken care of by then. Get a hold of a Tacoma scheduled service guideline and see if you can match up and see if stuff has been done.

As far as private or dealers it's a complete toss up. If you are comfortable with the dealer go chew on them for a while and see what you can get. These trucks are notorious for holding value though so be prepared for a fight. Bearings/ball joints, etc are the primary stuff you should be looking at. Major components should be in decent shape still.