Based on those comments, FFXIV would be my recommendation. As I say, FFXIV is probably not a great multiboxing game, but is a fantastic MMO in it's own right that also just so happens to be going through a "golden age" right now, with the community generally being very positive about its most recent expansion. There is the odd piece of group content that is compulsory, but its honestly not a big deal at all. PvP and gold farming are also not really big things in it, at all. The only bad thing I have to say about FFXIV is that you do eventually run out of content, it's not a game you could play 50 hours a week for month on end and still have things to do. But, if you're new to the game, that won't be a problem for the first 100-200 or so hours of gameplay.
In terms of "playing fun classes", FFXIV also has a system where one character can learn all the classes: the class you are using is determined by what weapon you are holding. So that's a plus if you're the sort of person that like trying every possible class under the sun in an MMO to figure out which one speaks to you.
In terms of a game to dual box, SWTOR stands out. The fact that you can bring along two companions means you can run with a "full" party to clear group quests even on a two-box. It's a pretty robust MMO with a reasonably generous F2P offering. If you've not played through the storyline before, that will be a reasonably charismatic experience. It inherits a lot of DNA from the old Bioware games with lots of good/evil story choices (think Dragon Age, Jade Empire, Mass Effect, etc), which might be a positive or a negative for you.
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