Quoted from hoov:
There was an interesting thread comparing manufacturers a year or two ago comparing Pinball manufacturers to Chevy, Ford, Dodge, AMC, etc..
You might want to go to a major show with a lot of em variety - think Allentown, TPF, Clay's, etc.. - and play different manufacturers from different eras to see what you like.
Gottlieb for me because imho they knocked the ball out of the park in the 50's - 70's with their rulesets, artwork, and quality. Plus, parts are interchangeable from era to era and easy to come by. Someday if one comes up for sale local, I want to try out a pre-1967 Williams that made my top 10 list to see how it feels. It's been too many years and I don't remember - most of the games where I played were all Gottliebs.
I find the car analogy to be a good point for these discussions. For many years (more so than pinball), I was an old car collector and saw the various owner cliques at the car shows. Always the Chevy vs. Ford vs. Mopar, etc. Most of the enthusiastic owners could lift the hood of the car and point out the factory correct work and/or "apologize" for the mods that had been put in over the years. Similarly, it was always fun to be friends with other collectors who owned different marques than you. While I was primarily a Chevy guy, I enjoyed driving and helping out on my friend's Fords. And, likewise, can appreciate how a well tuned, expertly restored example of a '67 Mustang is a more enjoyable vehicle than a "get-it-going" '67 Camaro...
I have representation of several different manufacturers in my collection and find it difficult to choose a best among them. The largest number is Gottlieb and for the reasons mentioned above and by me previously, availability, the artwork, quality and ease of working on them, etc. might take a #1 position. But, as we all know, it's hard to seek out specific titles and when a person has a game for sale (that is working properly), you absolutely need to evaluate it on it's own merits. A well tuned example of some "C" title game is a more enjoyable game than a mediocre playing "A" title game.
Williams - there are 4 in my collection, and each plays differently from one another and completely differently than other manufacturers.
Jigsaw and Gusher, are just a year apart (1957 and 1958) and are so different in game play and design it's hard to believe it's the same company. Jigsaw was the first woodrail that I got and a wonderful example of a game that has various ways to win, great artwork, kickout, rollovers, a guarded gobble hole, light animation in the backglass, etc. Gusher was the first game with a disappearing bumper - neat effect, along with nice artwork and game play. I also have an Official Baseball, not officially a pinball game, but it is a woodrail/arcade game that is a lot of fun. Last, I have a Nags, which is a pinball, but plays like an arcade game, and although a fun novelty game for guests and non-pinheads, with the rotating platter of pop bumpers, it is one that wins replays primarily by luck, and not necessarily by pinball finesse.
A manufacturer not mentioned by the OP is Genco. There are two in my collection and others in this forum have mentioned some of the Genco games in their collection. Admittedly rarer and harder to find, these are worthy of consideration, particularly if you can find one in restored or restorable condition. The '57 Show Boat is a great player - good card theme, lots of pop bumpers, carry over, one small gobble hole, multiple game awards, colorful art glass -it is very similar in play and activity to the Gottlieb games. The '52 Springtime is one of my most enjoyable games and incorporates a bagatelle into the backglass. Game play with the flippers and pops are to advance balls up an elevator in the backglass to load them onto a trough. Hitting a ball release rollover on the playfield releases balls as they are gathered in the trough to fall through 12 lanes. If you can light all 12 lanes, definitely achievable, but not often, you can get 20 games. Lighting less lanes awards less games, etc.
I have one Midway - also not mentioned by the OP. Flying Turns is not your typical pinball play - it is more arcade like that you are trying to advance cars around a lap and you don't win by scoring points.
I don't currently have a Chicago Coin or Bally machine