I don't want to sound like a salesman here and I am not 100% sure where we will be at with pins for sale this Spring but we are planning on selling a bunch of machines out of our collection sometime in 2016. We have a really nice Dr Who that will be going for sure as well as an F-14, Lethal Weapon 3, Pin-Bot, Black Rose, Road Kings, Space Shuttle, Checkpoint, and several other Williams & Data East machines that will likely be in the $1500 to $2500 price range.
Some might make it to Allentown but most will likely be sold out of our house in Carlisle PA (about a mile off I-81). Pretty much everything we will be selling will be working 100% and in better than average condition. Our plan is to sell off about 1/2 the collection to make room to remodel the basement.
We are no where near ready to show or sell anything right now but your timing might work out great if you are going to be shopping for machines around the time of Pinfest.
To answer your original question I don't think you can really miss with any of the Williams System 11 machines or the DMD machines that came right after System 11's. I don't think I have ever played a System 11 machine I didn't like and most Data East machines are in that same family. I know some people don't have a lot of love for some of the Data East stuff but overall most are still a good value.
If you have the space and can come up with $2500 to $3000 my suggestion would be two $1250 to $1600 machines instead of just one $2500 to $3000 machine. Regardless of what single pin you buy it will get old fairly quickly. Having 2 (or more) is better than one higher priced machine in my opinion.