Welcome. I was in your shoes just 6 months ago. I bought two early model solid states for $250 each. I learned the in-n-outs, put about $200 in to each and sold them for $1000 each. I bought two more entry level family-fun Sterns (Monopoly and Roller Coaster Tycoon) from a dealer with 90 day warranty (this is a good deal). Shopped both, tuned them, got them working perfect and my family is in love. I bought an older rare SS (Torpedo Alley) for $900 from Craigs list, put $300 in to it and its a keeper. I just picked up a Sega X files and nearly done shopping and modding it.
Like someone said, buy from Craig's List you will need to be brave enough to dive in and work on them. Owning is very difference then playing them.
Our friends and family love coming over now. We have slots, arcades and now four pins. I now solder circuit level components, troubleshoot lights and coil circuits, add modifications, etc. I love the hobby - there's more to it then playing.