How much are you looking to spend? and welcome.

You said you have been playing casually for a while. What games did you like. for example were they older pins from the eighties or the newer stuff like iron man? Personally i started out with a couple early SS games, i find they are a good learning tool for me, but its all in what u like and if your having fun,

Whoohoo then, I'm relatively certain that a number of the inmates here can fix you up.
Seriously, if you've played a few out in the wild and funds are not an issue, pick you favorites and keep an eye on you local Craigslist, the Market here, and Mr. Pinball Classifieds. If you don't have any favorites yet, go to the top 100 list here, review some ratings and find a few arcades or bars/restraunts that have pins and play some til you feel comfortable with the idea of sharing your home with one. By the way, welcome this place and good luck.
the other Skip

Welcome to Pinside, PW!

Are you mechanically inclined? Do you plan on working on the machines yourself? If so, it would probably makes sense to go with a simpler game to start with. A System 11 pin from the mid to late 80's would be a good choice.

A good place to keep up with machine value is both here on Pinside as well as here:

http://www.mindformation.com/pinball/ebay_sales_db.html

If you aren't picky just snag whatever comes up locally that is a fair value. Pins are an easy sell if they are priced near market value, and ratings-wise you'll inevitably find that some of the lower rated pins are the ones you most enjoy playing. If you don't like it just sell or trade it and go to the next.

Looking for a specific title is a recipe for frustration and/or overpaying in my experience. There are literally hundreds of fun titles out there. My only recommendation is to stay System 11 or newer, anything older lacks the gameplay to hold my attention. But that is only my opinion, there are many who will disagree.

That is really great news!

Take a look at AFM, White Water or TZ...you are going to be in for a treat.

I would start checking the local CL and see what you can find. anything really to get you used to opening it up, working on the mechanics, cleaning, etc. of course if price isn't an issue you could always go the tatman route.

I would recommend getting one that is fully working at first and learn to fix things as they break, rather then start with a fixer upper.

Yes, if money is no object, better to get a working machine than wasting time chasing down problems.

if price is not a factor you cant go past MM top of every list i have seen

Just start with anything you can find near you in person a start trading from there. Cannot go wrong.

+1. Find out what type of pin you enjoy (EM, SS, DMD). I found that I enjoy trading up for new ones to keep the game room fresh. FYI: Condition and theme is everything.

Welcome to pinside.

Find one with a theme you like in the top 30 or so in the Pinside rankings. My first was Fish Tales because I like fishing. Had there not been a game made with the "perfect theme" for me I doubt I'd be in this hobby.

I've got a STTNG going up for sale soon...

Find one that you want to sell to me when you're done, like AFM or FH!

However, where are you located? This MAY help your pinhead friends look out for deals for you locally...

I would agree with this. Where are you located?

Stay away from Gottlieb system 1 and 80 games.