First game should be HS2 and it can be found for 2k, although it quickly creeps to $2.5 for super nice condition or $3k if pimped out and nice plated hardware. I would suggest adding BK for second pin. Can find for $1k but that rises to $2k if new CPR playfield installed and $2.5k if pimped out in chrome hardware.
It doesn't really matter what price level you get in at because there are always buyers for a game at each level when it comes time to sell. It is probably better advice to suggest buying at the level that you want to be staring at after the purchase though.
I sold a GREAT HS2 recently, and while waiting for buyer to show up, thought how it is the perfect title for a first time buyer. Theme is family friendly while allowing dad to still feel macho. Game has great flow and is all around fun. I still have a nice black knight available though...It has very good flow (Steve Ritchie design) while maintaining a retro feel because of the timed drop targets and mechanical bell.