I was in the same boat as you two days ago, maybe I was a little better off having experience with video arcades. Check my post out "paragon" it shows my story of the last couple of weeks leading up to me buying my first pin.
Biggiest thing I can say is condition.... Condition of the game as a whole and condition of the parts that make it playable. If your handy and don't mind spending a few c notes any game is fixable. (And with the Internet you can find the knowledge you need to fix it... This forums the best source)
The game I bought isn't working, same as the play boy your looking at, it lights up but nothing else. My MPU is fried, I could spend the time and fix it but I opted to buy a brand new board and be done with it. With misc. parts and the time needed to actually repair a board I say it goes to be about $100-$150... A new board is $200...just depend what value you put on your time...
Good luck keep us posted if you get it!