Steve,

For that price bracket I would seriously consider a Last Action Hero.  Dorky movie, but the game is super super fun.  Its actually the sister game to JP.  Modes are similar, but 6 multiball, 3 massive magnets which cause mayhem and a big old crane in the middle of the playfield to move the locked balls!

You'd pickup (maybe) a WH20 privately....MartyMachine is selling one at the moment which comes with lots of extras.  That would be worth a look if it hasn't sold.

T2 is a great game, but you would struggle find at under $2500 at the moment.  Getaway is a blast.

Everyones's tastes are different.  I would definitely suggest getting them to put a few hours in playing different games to see what grabs them.  You don't want to buy a pin based on a theme only.

I think MarkC was talking about a meet soonish, which is a great opportunity to test drive and see heaps of different games.  Or pinball faith at Bumper.