I have been playing dwarf fortress for about 7-8 years. If anybody has any questions feel free to ask me. I think the difficulty of learning the game is overstated: if you follow a tutorial, use a graphics pack, and use dwarf therapist (dwarf therapist is a must, most experienced players also use this because it's just a better UI) I think you can get the hang of the game in a few hours of play time. Probably the big…
here's where I struggled: I still wouldn't have the hang of managing the dwarves I had and then a new crop would come along. Even with all these tools it quickly descended into me not having any idea who was doing what or why. Or why they weren't doing the things I was asking them to do.
A lot of the things seemed way too roundabout to me too. Like I'd have chickens (or were they ducks? I forget) and I was attempting to breed them. But the whole process of making egg-laying boxes or nests or whatever was tedious and then you had to lock the door to stop the dwarves coming in and taking the eggs.
Likewise, i found the process of feeding the dwarves hard to manage largely because I couldn't easily figure out if there was any food, whether that was because no one was making any or that it was simply all getting eaten. Was it an issue of not having room to stockpile food? Or was the dwarf who could make food doing something else (possibly because he was the only person who could do that or he just happened to be the one who'd picked up the pick for some reason)?
So I never got to that point where I felt like I had a good grasp of my colony as a coherent unit and could then engage in flights of fancy.
I think the last time I tried I then got a monster invading and I hadn't figured out military yet. That was a whole new system to learn and I just lacked the motivation so stopped and never went back.