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My first real hurdle was becoming a Mahler-ite. At the beginning (meaning when I started really getting into classical music, at age 12-13) I didn't know anything about him but his First Symphony, which I tended to confuse at times with Beethoven's Pastoral or Ninth. But within a year and a half I got to realize how wonderful his works are, even if long. As of now, the only work by him I still struggle with a bit is the Third Symphony. Next step was Shostakovich, which I took a bit longer to love. But I totally do now. Prokofiev was never that hard for me, though. I have begun to come into terms with Alban Berg lately, but I still can't stand most of the atonal/serialist/modernist guys, no matter how long and hard I've tried. Let's not lose hope, though!

If you had asked me 3 years ago my opinion of the likes of Scriabin, Prokofiev, and heck even some of the guys here on YC, you would have gotten a flat response at best. But it didn't take too long for me to start liking it more and more. It seems to me that the more I listen to something (assuming it has any merit to begin with) the more I can appreciate it. If I understand what you're getting at correctly, I think you're right. I think the music that is the most special to me is the music that took me a bit longer to get into (mostly, I mean does anybody really need a second listen to love Tchaikovsky?). There's a feeling of satisfaction after having learned to appreciate something (it's as if you actually did learn something) that can surpass the feeling you get when you like something right away.