Monster Bashr

With your budget I would try and go for two pins. One pin set up is tough, sometimes a pin is just a bitch and you can't get anything to go on it. Being able to just go, ok your shit today lets try this one right next to you. That one will play like a dream. When you stuck on one it can be frustrating. No matter how great a pin is they tend to multiply so its good to have a little reserve in the pin fund.

Don't be afraid of an older pin as far as maintenance I find a pin is a pin and they all require about the same amount of tuning and tweaking. So long as its in decent shape your probably safe. Overall they are very reliable.

Get 3 and rotate them every year. You could get 2 early 90s DMD and 1 80s System 11.
Pick 2 from Column A and 1 From Colum B. All are in the top 150. Get one a month for the next few months then trade one out every few months. You should be able to about break even on trades every time as long as you don't go nuts fixing them up.

A
Fish Tales
Last Action Hero
Jurassic Park
World Cup Soccer
Roller Coaster Tycoon
Monopoly
Judge Dredd
Road Show
Revenge From Mars
Ripley's Believe It Or Not
Doctor Who
Johnny Mnemonic
Terminator 2
Stargate
Black Knight 2000
Dirty Harry
Baywatch
Demolition Man
No Fear

B
Pinbot
High Speed
Fire
Flash Gordon
SeaWitch
Firepower
Cyclone
F-14

Get a modern game you enjoy now. If you get tired of it in a few months sell it and buy stuff much different than your first game.

As you get into the hobby you'll learn what you enjoy. Get involved in your local community to experience more aspects of pinball like competitions and learning to maintain your games.

Some other older titles that are great but not mentioned:

Tales from the Crypt
The Shadow
Bram Stoker's Dracula

MBr

It depends on if your going to learn to fix your own games.
If so I would start with some early ss Bally and Williams games first.

Out, while you still can.

F14 Tomcat

Check http://pinballrevolution.com/ to hook up with the local supply!

If you have space I agree more than one pin would be better. We used to have 10 or so then we were forced to scale way back and dropped to one pin and a VPIN. The VPIN has been great and its staying but I am always working on it and it cannot replace a real pin. That being said we are adding some pins back into the house now and will be at 3 + the VPIN.

Also having more than one game allows for different types of games. Some games are crazy fast fun, others are deep long ball times and marathons etc. You really need a mix of kinds in your game selection to allow for longevity.

For us we plan to get to 4 + the VPIN. Spot #4 will most likely be a constant rotation game i.e. every 6 months to a year sell it and get something else. The keepers are MB, JJP-POTC, and we are working to acquire our very first pin back into the house as the wife wants it and that is Silverball Mania. If I had more room and more money I would love to be back at 10 games but that just isn't possible.

So an older SS game and a newer DMD game I think would be a great place to start based on budget. Folks have already listed some great choices so nothing really I can add to that list. Good luck with your search and welcome to the insanity, I mean addiction, I mean torture err... welcome to the hobby!

It doesn’t matter what you get...if your hooked like you say then your in trouble.....should have just tried heroin it’s probably cheaper

MONSTER BASH REMAKE

Taxi , wcs94, and woz are good favorites of non pinball and pinball players alike. Your buddies coming over might enjoy tna

I recommend also getting a project EM to putt around on. It's a steep learning curve but very rewarding.

There are so many good ones but i agree with others that say get more then one. Got my first one a year ago and will be getting seventh one tomorrow. Love a variety instead of one expensive one.

Great first pin, it was mine as well. It’s big I think heavier than your average pin. Two great diy mods are lighting the back of the playfield and lighting the Trex scoop.

Congrats. Great first pin!

Nice job it’s a great game. Ironically it was our first dmd pin in our house. Wish we still had it. Have fun with it

Good choice. I was just gonna say to not limit your options. New pins come with quite the sticker shock nowadays so I always recommend people start out with games like Flash, Meteor, Firepower, Space Shuttle, Pinbot, etc. JP is a fine choice though. Best of luck to you.

New batteries
New pinballs.
New rubbers and clean the playfield.

There's an add on here right now for 2 NIB Metallica and aerosmith pro for 8500 for the pair