Truck hunting,whacha got??

My son is looking to buy a truck. I have tried to talk him into something older like 60's or 70's, but he wants something from the 80's to mid 90's. He has a budget of about $5000. If I am going to haul it up from the US I would have to get it for around 3-4000. Here are some of the specifics he wants.
1. Any make, he doesnt have his heart set on any 1 make.
2. Extended cab or 4 door
3. 2WD or 4WD

Thats about it. This is his first vehicle so I am trying to find him something fairly reliable. I tried to persuade him into something older as that way I can help him with most repairs etc. With the newer vehicles that wont be the case and it will be going off to the garage for any repairs, so that will suck up his $$$ money quick at $70/hr. Thanks guys, hopefully I get some feedback to see what is out there for price and for make.

Thanks
Steve