Because the game is progressive, the players must, I think, progress in their approach. At first the challenge is just learning the game -- what each icon does and what you need to do to get through the first 5 chapters. Then comes the challenge of learning how to do the Guest Races, Tournament, and Spire all at once. Finally, as you get to a certain point around chapter 10 or so, you move into a different attitude. Having mastered the basics at the beginning, the guest races at the middle, and now learning how to do the various military or catering challenges while still moving ahead, you, in the end, come to the place where you've pretty much mastered all that. At that point you have to be more competitive and/or "outgoing." In other words, you have to start considering your rank and the rank of your fellowship -- more competitive, and/or you have to find your focus in the people you meet.
I'm in Chapter 18 and there are few challenges I can't meet pretty easily. However, while that does make the game a bit tedious, it doesn't mean it's not fun. My fun comes from three sources. Leading my fellowship; moving my fellowship toward goals; and the forum. I believe most players, in the end game, find these things more fun than the game itself. Not all end game players, of course, but most. They simply find their fun in the players instead of the play.
But here's another idea. Sometimes it's tedious because you spend too much time on it. If you have one city this is less a problem, but if you have three, four, five, six, seven...or more .... I imagine it can be very, very tedious and rapidly become boring. So, in my opinion, most players should have three or less cities and if they start to get bored, focus on one. Then get involved in your fellowship and interact.
I'm not sure how Inno can help with the move from game-skills based playing enjoyment, to people-based enjoyment, and maybe they can't, but anything in that direction would certainly help in my enjoyment. Like in game recruitment help, wider chat abilities, multi tabbed mail system (with personalized lists of players so you can set up mail groups). In other words, better player communication options for the most part.
Anyway, I hope this helps you find some fun again. Otherwise, I would also suggest a long break might be in order.
AJ