sunshinecorp: I prefer the 1st and 2nd editions as a whole (especially since the 1st is paradoxically so well supported these days by open projects like OSRIC and several adventures are still being published by the likes of DCC) but if you want something modern, stick to ed. 3.5 (d20). I'd stay the hell away from 4th and I didn't really enjoy 5th either.
That is interesting, I feel the same about the good old editions. AD&D or Second Edition was a superb system, you could play it as an encounter-based combat game (Baldurs Gate) with light roleplaying or as a fully-fledged deep roleplaying character-based making-stories up game were the numbers served as guidelines.
3rd Edition was very system-based, very well suited for character optimization and video games, the whole notion of character builds started there. Problem is, it detracted from the roleplaying aspect in my opinion with all these classes, feats, talents, prestige and the whatnot. Did not touch 4th edition since the ruined the Forgotten Realms :-)
HOWEVER, I am absolutely digging the fifth edition. It is almost like in the good old days, just with much more elegant better mechanics (THAC0, I am looking at you).
It is
very elegant, it is extremely flexible and it refocuses on what made the AD&D great. It is less number-crunching and character-build based and instead gives the dungeon master the freedom to adapt the system to whatever he or she needs instead of having to limit players to a managable level like in 3rd.
If you require more strict rules to keep the game going or prevent arguments, you will need to decide on these beforehand. The Dungeon Masters Book gives you many good examples of how to do things instead of dogmatically declaring how to do things. In short, 5th edition gave me back D&D. To quote GameStop: "Power to the players".
To answer the main thread question, it is
somewhat easy to learn for a pen & paper RPG. Definitely easier than 3rd or 2nd edition. If you have a good DM that is, it always depends on the DM. All you really need to get going is the Player's Handbook which contains everything a player and a sufficiently creative DM needs to play.
Note that the beginner's box is a really lousy start, focusing very much on difficult combat encounters. A good DM with a creative initial adventure is much better.