I myself am still just getting started in pinball collecting and everything but have learned a TON and here's some things I can share with you, LoserKid3:
1. Prices are determined by five factors: Age, Upkeep, License, Playability, and Rarity. Age is a very minor factor but typically, older is cheaper. Upkeep is a very MAJOR factor, thus if you get a steal price on a pin chances are its condition is far less than perfect (if it's even working). Licensed pins are often (but not always) much more expensive than unlicensed pins just because of the license. The more playable a pin is, IE: the more stuff there is to do and the less one-dimensional it is, the more valuable it will be out of the desire to actually play it. Any pin that's had 2000 or more made typically isn't very rare and its value won't be affected as such, but any pin with very low production numbers, particularly below the 1000 mark, will be more expensive just because of how rare it is. Price can also be determined by the number of custom-made parts inside, though usually the machine has to be fairly popular for this to play a major factor, such as Attack from Mars and Monster Bash which are both loaded with toys inside.
2. If you're buying a machine to "flip" like a house, forget it. If you buy a working game you'll never get back what you put in, and if you buy a non-working game by the time you get it working you'll probably have spent more on parts and shipping/gas than you'll get in return. That said, if you keep it in good shape, it'll still be worth a decent amount if and when you go to sell, so instead of looking at it as an investment you'll see a return on, look at it as an alternate place to stash your money that will offer fun gameplay in the process. ; )
3. Listen to vid1900. Always. ; D
4. Avoid eBay for buying full machines. Chances are the prices on the machines you find will be MUCH higher than they should be. Not always, but most of the time. Parts you can sometimes source from eBay for decent prices if you need something specific and can't find it from one of the major online pinball parts stores.
5. Be prepared to carry wads of cash if buying local. : B
6. There are two extremes when it comes to pinball people: Those who primarily enjoy playing and those who primarily enjoying tinkering. Depending on which kind you are, or if you fall in the middle somewhere, will determine how much you should be spending on your pins. (Not to mention how much space you have, how much money you make, what your wife/kids think of the notion, etc.) If you just want to play and don't want to tinker, spend more and get fully working machines that have been overhauled and everything, or Hell, buy NIB and end up with something that will have very few issues. If you mostly want to tinker, go ahead and buy a non-working machine for dirt-cheap and see if you can bring it back to life, though most people would recommend you never buy a project machine as your first.
7. The ONLY surefire way to make money on pins nowadays with minimal effort is to buy into a brand new LE run, then leave it sit for a couple or so years and resell NIB. Whether or not that's a good or bad thing depends on your point of view. Me personally, I can't fathom the notion of buying a brand new pinball machine JUST to keep it boxed up to sell later on; I'd want to play it! ; D