When considering a first pin, your best money is spent AFTER you go to a show OR join a local league and play 50-100 titles more than once. A lot of people really think they like a game and after 10 MORE plays (after they buy it), they realize it's just not for them.

Whitewater may be priced around a NIB Stern but certainly not Getaway. Both are good games but I tire of Whitewater very quickly and Getaway never gets old.

You can get a decent HS2 for 3K or less.
You can buy F-14 Tomcat for 2K or less.
You can buy a bunch of classic late 70's-early 80's Bally's or Williams machines for under 2K.

2 of these classics hold up better over time against a single Stern machine but that's just my opinion. You need to actually play them for yourself.

To some extent, I agree with the idea of a MB remake. It's the better buy right now for NIB. Try to play one 20 times and decide that way before you lay out the money and have to resell for something else because you don't like it.

Also, Barcades with pinball are near every town these days. Go play some location games for 2-3 hours.

Whatever the path you choose, make certain you play the hell out of a game before you decide that it's the one you are taking home and you should be fine. No one on here has an opinion that is better than yours about what game(s) you should own.

Also, there is a price guide of sorts here that tracks sales but it's not always super current/accurate: http://www.bostonpinball.biz/eBay112118.htm

Sounds like you're headed in the right direction. If you really like playing on location take it another step and try playing in a local tournament to meet other enthusietsts. You may really like it.