Definitely don't overplan, and I would advise against buying multiple pins off the bat, start with one that you really like and go from there...I think a little variety is good in manufacturer, time period and designers; especially in a smaller collection.

Also, you'll probably want pins that have different types of layouts and gameplay; and that takes time to recognize and appreciate; so take your time and enjoy.

I will add, that when I started collecting, I was looking at modern Sterns all the way; my first pin purchase was a D/E DMD; but as time has progressed, I have gravitated towards the 90's B/W's; they are just the best feeling to me; and I appreciate the simpler modes of play on them compared to modern pins; it's all in the evolution of me as a pinball player and owner.