As I think about this and all of the other MMOs I've played (which is a LOT), I think the core of the challenge are two fold.
1. The leveling experience. This is an area that I really enjoy in most games. However, most of the current generation MMOs have the same leveling experience, regardless of what character you play. That is, the quests are basically all the same. The one exception to this recently was SWTOR. Unfortunately, the game mechanics were so much like WoW that I was kinda burned out on it just because of that. Other games, the leveling content is either too easy, too fast or not varied enough to really support having multiple toons or lasting long enough for a a true "main". This is a large part of why I've played so many MMOs, is that I level up a toon, have a great time, then hit a wall at the end game and because there isn't good repeat-ability, I get bored and basically burn out.
2. Group content. Unfortunately these days for me, group content can be a problem. The first challenge I have is that most all of the friends that I'd really like to be playing with all have interested in other games or have odd play times. Back in the day with EQ, there was one game in town, so EVERYONE was there. These days, everyone has their own favorite game and it can be difficult to pull all your old friends into the same game and get them leveled up to do "end game" content. Similarly, most of the current breed of games don't do side kicking or mentoring, so if you don't "keep up with the joneses" you're basically playing alone. Lastly, which is kind of an off shoot of the last point, is that most all of my friends are adults, many with children and all with decent paying jobs and responsibilities. The days of spending ALL DAY Saturday raiding Fear are long gone. Hell, for me personally with my travel schedule and other interests/responsibilities, it's very hard for me to even be able to commit to a planned raid time, much less do it regularly. So while I'd love to do group content, it's almost always hard for me to manage it, so I end up playing alone a lot because I can't commit the time.
In the end, I think the reality is that we're all older now and the magic of the past doesn't really work well in the present. As much as we'd all like it to.
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