Same as Antimatter I have no tabletop experience and only know D&D from the video game adaptations.
I would probably have agreed with
@Fandraxx about the 2nd edition, but in the end I have come to the conclusion that it's simply the ruleset I'm most familiar with because of the Baldur's Gate series, and it most certainly wasn't the easiest to get into in the sense that I knew what I was doing for quite a while. (think Thac0, and spell schools with all their odds, and far too many saving throws)
Class restrictions made it complicated and a well-balanced party was a must, on the other hand you didn't need to worry much about builds, except for where to put your thief skill points or weapons points.
3rd edition, or what I know of it from Neverwinter Nights, gave more flexibility, but made it very, very complicated for me. All those multiclass options with a level of this, a level of that for all those bonus things you get, only to find out then that you should have invested one more point in DEX to take the next one in that branch, or that you miss one other choice to be able to take that prestige class... that's where the encyclopedia of build optimization started.
Which you don't need in a tabletop game, I assume. But in a computer game that gives you only one restricted henchman, or that lets you play on a variety of multiplayer servers (which I have never done), it can make quite a difference.
5E? No idea. I have seen a bit of BG3 Early access gameplay of course, but not enough to form an opinion (and the way that is going, I'm not buying it before release), and I backed the 5E campaign book Raiders of the Serpent Sea on Kickstarter, but as
@Brent Knowles said in his thread
about it here, apparently 5th edition is easier to get into than the older ones, so I'm looking forward to seeing how it works.
And since Fandraxx said 5E gives more room for roleplaying, that sounds good to me too.
One issue I have with D&D rules in general are the dice. Yeah, yeah, I know, people whining about unfair dice or incorrect odds appear all the time, I don't mean that.
In a game with friends, this random element of chance is fine, adds to fun or frustration and evens out the chances a bit.
In a video game, especially when it comes to fights, I prefer a tactical approach, not a game of chance. So while I need to be careful at lower levels, there's a point in a game where I would like to control the fight or fail it through application of my skills, ideas I have, calculating how the enemies might react and prepare or counter accordingly.
What I don't like are "save or else" scenarios, where I survive only through a lucky saving throw, or where the whole outcome relies on lucky dice rolls that I might repeat a few times for success. If luck hits, I'll take it of course, but I want to find a solution that makes it possible to succeed without save-scumming.
What especially bothered me in NWN 3rd edition were critical failures. I get it that no matter how honed your skills are, mistakes happen and perfection doesn't exist. But please, what's the equivalent of rolling a 1 and missing when we're talking about a highly trained fighter being able to fight blindfolded but missing a hit with a hammer on a big unmoving object? (I know, critical misses could be deactivated. I did.)