I still think there is good value in those $2,500 DMDs. Just looking over the top-100: The Shadow, Bram Stoker's Dracula, The Getaway, Fish Tales, Road Show, Judge Dredd, World Cup Soccer, Jurassic Park, Terminator 2, Johnny Mnemonic, etc. all seem like you might be able to find them in that range. But there really are great games in all price ranges, so my suggestion is to make several lists and see what turns up in your area.

Monopoly has a unique layout with a lot of toys. I like playing it on location, but it doesn't get the adrenaline pumping like Bram Stoker's Dracula (BSD). The appeal to BSD is that you're almost always a few shots away from a great game. Games are fairly quick, so you can keep hitting the start button and savor the moments when you start hearing Dracula saying, "10 million!", "20 million!!", "30 million!!!". I've owned many of the games I listed. Of those, Jurassic Park was the one played most often by friends. It has a good theme and one of the best toys in pinball. Despite that, I sold it off and brought in a Fish Tales. Another one of those games where you're always a few shots away from a great game. I actually like it more then BSD, but I'm probably in the minority there. I just really enjoy those crossing ramp shots. Seriously though, the best way to decide what you want is to play games. Personally, I like quick and simple games.