This is what I have seen lately in this area.
You can get machines such as JP, Demo Man, Johnny Mnemonic, maybe Simpsons, and a handful of similar titles for $900-$1200.
Then there is a gap for Nightmare On Elm Street, Last action Hero, quality machines for $1500.
Then you get to $2000-$2200 starts at themes like No Good Gofers, Teed Off, earlier "New" Sterns.
Lastly you have nice classics such as Addams, Theater of Magic, and Sterns from the last 2-4 years.
I have saved up some cash to buy a real nice pin, but what I have found is that I am really looking at the $800-$1200 machines as fun, but not over the top, or a nice high end pin like Theatre of Magic. To me, there is a void of pins that I am interested in at the $1400-$2000 range.