I agree with DirtFlipper that it's a slippery slope.... The wood rails are a very different league than the EMs of the '60s or of the 70's. Each EM era has a unique charm. Looking at the machines in your collection, you'll certainly agree that a modern Metallica is a world of difference than your Ice Review.
I will be the first to admit that the woodies, generally, aren't as much "fun" to play as later machines. Small flippers, wide gaps, monstrous gobble holes...they were clearly set up to favor the vendor. Winning games is hard, but were achievable. Many woodies allow you to win not only by scoring a certain amount of points, but, additionally, had different kinds of Specials that could award up to 10 replays. (Actually, my Derby Day discussed in another thread, could award up to 12).
Consider, though, that it's going to be a challenge to find any of the six machines that you mentioned in the first post. I am most familiar with a Dragonette and would like to find one, too. Closest I got was seeing and playing a nice one at the Allentown show a few weeks ago, but the machine was not for sale. Some machines that you read about in the forums are so rare and desirable that they hardly go up for sale. And, you are not alone in looking for games with "great art and game play," so if a candidate does show up near you, you may have company bidding on it.
I'm familiar with the games that DirtFlipper mentioned. I also have a Criss Cross, currently being shopped, and have a friend with a Queen of Hearts and a Sittin' Pretty. I would endorse them, but again, they are hard to find.
Besides the '58 Gottlieb Criss Cross, I have a '56 Derby Day, '59 Miss Annabelle and '57 World Champ. Also have a '57 Williams Jig Saw, a very good game with beautiful artwork, but not a Gottlieb, as you asked. These games became available for me when other collectors decided to part with them. It wasn't as if I was specifically looking to find any of them and I jumped on them once I had a chance to see them in person and play them. I'll mention, also, that I did see some beautifully restored games from the early 50's that I passed on: these games had impulse flippers, or reverse flippers, way too many gobble holes, etc. Nice to look at, but not much fun to play. To this, good advice is for you to touch and play the machine you buy. Be careful about buying something that other people might like, you may find that it isn't to your liking.
In my collection, the Derby Day is my favorite machine for play. Actually easier for me to win on Miss Annabelle or Criss Cross (the late 50's games had the pop bumpers closer together, so higher scores were attainable), but the Derby Day has several ways to win multiple games at once and a big pop bumper below the flippers to bring a ball back into play. It's a game that can be nudged and banged and skill shots galore. Miss Annabelle has the nicest artwork, but no specials, per se, and is not my favorite player, but it is for one of my friends.
IMHO, in my collection, the best combo of great art and great play is the World Champ. Beautiful art and winning multiple games with specials isn't that hard.
But again, the best playing 50's game is no where near the speed, pop and bang of a Cross Town, or a Slick Chick, or a big flipper game like El Dorado, etc. The woodies aren't for everyone, but for this 62 year old collector who grew up and worked in arcades, they are among my favorites.
Good luck with your search.