Gregory Oatmeal said:
First no one said that. That's silly. But really, divisions give me headaches and mean I constantly have to switch between different 300 page rulebooks whenever I play D&D. They're all just an impediment of rules and resources and disparate backgrounds that make it harder for the group to do what we all want to do. Do you have no sympathy for that?
Quite honestly? No. None. There have been divisions in D&D since I started playing in 1980. You had people playing Basic/Expert and people playing AD&D. And those were two very separate and distinct groups IME. And, additionally, the rules are not the same between those two games. They are pretty different in fact and the game plays pretty differently.
When 3e came out, I didn't make the switch immediately because I didn't see the need to. I had people who wanted to play in my 2e game and, after 10 years of playing 2e, I could run a pretty decent 2e game. Then I played in a 3e game and never went back. I thought it was a better game. It took all my house rules, made them ten times better and then gave me more stuff.
Then, by about 2005, I had realized that I didn't have the time to prep 3e games to my satisfaction and started running nothing but modules. I'd still run 3e, but, only with modules. It's not a system I care to homebrew in because it takes too much time for me. And, I'm not about to go back to 2e (partially because I no longer have those books - moving to three different countries on two different continents are HARD on gaming book collections

) because I no longer want a game with that kind of ruleset. It's no longer to my taste.
So, 4e rolls out. I wait a year or so to jump into 4e and again, I find that it appeals to my tastes now. It's much faster to design for - I can start making adventures again YAY! - it runs pretty sweet and it has some of the bells and whistles that I've learned to appreciate from playing other, more narrative to be honest - games.
However, all that being said, I've loved every edition that I've played, despite not wanting to go back.
Your presumption of an Evergreen D&D presumes that people's tastes don't change. I think they do. I don't play the way I played when I was 14 years old. The game that appeals to that 14 year old version of me is not the same as what appeals to me at 39.
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That all being said though, I do agree that D&D needs a solid gateway game. But, IMO, an RPG is not it. I'd go with a Euro-style board game with roleplaying elements. Think Diplomacy with a few more rules and more dragons. I always thought that the D&D Minis was an excellent gateway game to D&D. The gateway game to RPG's should not be a straight up RPG. Your Monopoly model actually would have better legs if the gateway game was an actual boardgame with RP elements.
Again, it's not 1982 anymore. It's not like there isn't a whole library of games on the market right now that could serve as a template for a D&D gateway game. We're not stuck with stodgy old Parker Brother's games of chance anymore. Catan, Rio Grande, Carcassonne, and others make a very, very good entry level RPG game.
Heck, D&D done with Dread rules would make a FANTASTIC gateway RPG game.