Basically I started early with pinball, bought a WMS Fan-tas-tic in about 1980 when I was about 13, traded for a Fun Land, then a Mata Hari when I was 16. My family was in the biz, new machine sales through Rowe Distributing in Toronto, and on location games, even venturing into "Magic Fingers" coin operated vibrating beds in motels. So I was no stranger to coin op. They were always around. I ventured in and out of the hobby many times over the last 40 years, going years without any at all, 15 years with just one (and the same one), up to about 35 (too many to enjoy), now trying to hover in the maximum of 10 range. Ideally 5 or 6 would probably be fine. I have no real preference to era, woodrails are an important evolutionary piece of the pinball puzzle, which allowed us to have todays modern flashy games. New games are pretty cool, but can be pretty "ouch" expensive.
Pinball is fun and pure, and a true art form, and there are plenty of less responsible ways to spend your hard earned cash. Enjoy all of it. Peace pinball brothers and sisters!