Quoted from bwill:
Should I look at places other than Pinside? I've checked out ebay and cl and the prices seem way off from what I see here. Are there other reputable markets places that are safe for a newbie?
You're in a good-sized city so it should be possible for you to buy local. That's definitely your best bet. Even if you end up paying a bit more for a local machine, you avoid hundreds of dollars in shipping fees and most importantly you get to check out the machine before you buy. If possible, find a local Pinsider that will ride along with you to kick the tires on a game or two. Someone with even a bit of experience can help you spot issues you'd probably miss on your own.
Of course if you've got your heart set on one specific machine you may not be able to buy local. I ended up buying my first machine through Pinside since I really, really wanted a Shadow and none were popping up in Denver over the six months I was looking. If you go for a long-distance sale, Pinside is IMO better than Mr. Pinball or other options because you can check people's posting history and if you buy from someone well established here they've got some skin in the game of maintaining their reputation by not totally ripping you off. That said, get lots of pictures and ask lots of questions before you pull the trigger.
Prices on eBay will almost always be way high, they have to cover the fees plus the buyer protections are pretty risky for selling and shipping a big item like that.
Quoted from bwill:
Are the estimated values on pinside a good guide for the range I should be willing to pay (roughly)?
Meh -- Estimated Value gives you an extremely rough range, but I think you're better off doing a search of recent sales of the game and then making your own adjustments for condition, mods, etc. Any sales from more than a year ago should be taken with a grain of salt, as prices do tend to move around (usually up, unfortunately).
Bring a flashlight in case they've got the game in a dimly lit area. Don't be shy about examining the game carefully, even if the seller is trying to rush you. You get one shot at inspection, so take your time.
Turn the game on and play a few games. Make sure that the lighting (backbox, above-playfield or "general illumination," and inserts) is all working. Play a few games and confirm that everything seems normal. If it's a DMD, look for a "credit-dot" (do a forum search if you don't know what that is). May be insignificant, may be something big, but if it's there you'll want to figure out what's up before you buy.
Take the glass off and check the playfield and ramps closely for wear/damage. It's so easy when you're excited about buying a game to overlook stuff that'll disappoint you later.
Also look very closely around and especially below the battery holder to see if there's corrosion from old leaking batteries. Even if the battery holder has been replaced with a remote holder or NVRAM, look where it used to be. This kind of damage can be easy for beginners to miss (ask me how I know) and can cost you hundreds for board repair or replacement. Do some searches on Pinside and you'll find example pics that can give you an idea of what to look for.
Pointing issues out to the seller may or may not get you a break on the price, but at least you'll known what you're buying.