For the record: I loved leveling in this game but once I reached 80 and got yellow gear across the board suddenly there was no real goal from there in sight. This is the game's flaw not the guild's. However wonderful the ideal of questing and solving jumping puzzles was to A-Net the sad truth is the gaming community as a whole needs challenges where it takes a lot more people to accomplish them. Maybe even to the extent where we have dependencies on other classes as well. I know this harks back to their arguments of what they wanted for this game....but if others (like us) are not playing then their argument and reasoning is flawed...this game maybe everything people asked for....and nothing close to what they really needed (which usually amounts to something very difficult and involving a lot of people to get.) See my point? So the problem for us is how to make something that is too easy and make it attractive for a number of people large enough to even call a community.
My best guess to help us is to go or focus on WvW. PvE is all but solo-able material except for dungeons. I hate (to a certain degree) WvW. HOWEVER, win or lose I always love the attempt when in the company of guild-mates who do their best and are mature. I would show up to lose everyday just to play with good people....FOR FUN! See my point here as well.
So to solve this thing about the game that is too easy. My advice is to move to the very hardest things about the game and direct all good people to it. WvW first and foremost...then when in PvE mode it would be Dungeons.
If we don't direct people now to the hardest aspects of this game and I mean now! Then all that is going to happen is they will run the gambit of the easier stuff....get bored and then run off and play another game which is more challenging and requires more people.
Will this be easy to do....hell no even I don't want to WvW...but I'm smart enough to know it's what I need / we need.... vs....what I would perfer or asked for.