Depending on space I think the smart move is several machines under $1000 if you have the room. Pick on titles that are not as popular and you can grab some fun machines reasonable. Some off the top of my head are: for under about $750 to $900 you can likely buy --- Spring Break, Shaq Attack, Firepower, Gold Wings, a lot of Williams system 6 & 7 machines and most Gottlieb System one and eighty machines. If you step it up to $1200 to $1500 you can get a good many of the William's System 11 titles as well as a good many Data East titles.
Why buy just one machine for $3000 to $5000 when you can own 4 or 5 for the same money? That is providing you have the space for them.
I don't care what you buy if you only own one or two machines you will get sick of playing them. If you own a half a dozen to 10 machines there is always something different to pay.
Just my 2 cents on things
If you don't mind a bit of a drive and you are not in a huge rush we will have a dozen (or more) shopped & serviced machines for sale in the Spring. We are selling off some of our collection getting ready to remodel the basement. We are in Carlisle PA about one mile from exit 45. We will have mostly machines in the price range of about $650 to around $3000