Rockwall, TX
You have clearly put some thought into it, and that's a great first step. You are already ahead of most. Here are my recommendations on where to go from there:
1. Play the games first:
I would first suggest you make mention on here of where you are located. It will help others connect with you and help you seek out places to play pins. It may also get you into private collections otherwise unaccessible. This is valuable because playing a game is massively important when deciding on what you (and your family) will like. If possible, go to nearby tournaments and shows for even more exposure. Your next best bet would be to watch gameplay of them online, but this is a distant second to playing them live.
2. Go for what YOU like:
As a family man myself (I have 3 kids), I can tell you that children have very different interest levels than you will. They may lose interest quickly, play one game a month, or not even play at all. This applies to spouses and friends as well. Buy for yourself first, but try to make it as accessible to loved ones as possible. If you do this and your family loses interest...you will still have something you can enjoy.
3. Don't worry about what others say:
If you like unpopular pins...so what? If you want an E.M., go for it. Find what works best for you.
4. Price and availability trump all:
I probably should have put this at #1 (not that these are in order). Unless you have limitless funds, the dollar amount will come into play at some point. There are certainly better values in some areas than in others, even by just sweeping over the pinside market a few minutes ago. You will also have to consider what is available. Some pins come up a lot, but some VERY RARELY come to market. Your patience level could be tested in some cases.
Final thoughts on specifics:
SantaEatsCheese gave a really well thought out answer. I would go back and read it again. My thoughts would be pretty similar.
For a newer pin, there are some fantastic family-friendly choices. Willy Wonka, Deadpool, Batman 66, Stern Star trek, JJP pirates of the Caribbean, Godzilla, Dialed In, etc. Your mention of WW would make me inclined to say go with that one, but I would take a little extra time to check out some of the others just in case you missed something.
For the DMD era, I really have a tough time not suggesting getting an Addams family. You really seem to have some fond memories of it, and it is a great game. I know you have a rocky and Bullwinkle coming, but you should at least consider it. Others options could be Lord of the rings, the Simpsons pinball party, or even a remake (medieval madness, attack from Mars, monster bash, cactus canyon).
As far as EMs go, I prefer drop Target games, so el dorado or joker poker would be pretty high on my list. You should also give consideration to early solid state or possibly even alpha numeric games in this spot. Early classic Bally's are incredible. Williams system 11 games are tons of fun for AN games. I can't say what you would like more, but I would definitely recommend looking into things like eight ball deluxe, fathom, flash Gordon, paragon...or pinbot, whirlwind, high speed, taxi, or even funhouse for alpha numerics.
