I first bought my copy of The Silmarillion in June 2002. I think it was a result of joining the Barrow Downs. Before joining, I hadn't really even heard of the book, but it was so talked about on the Downs. I felt absolutely clueless in some discussions and decided it was necessary to read it. Besides, I was curious. I read the first chapter and admit I found it incredibly boring. I didn't attempt to continue and instead got myself distracted by another fantasy series I still enjoy. I didn't pick up The Silmarillion again until the beginning of 2003- I decided that it was time I finally read the darned thing.
Getting through The Silmarillion was tough- it took months to finish it. Perhaps my difficulty with it was partially due to my age, after all I was only fourteen at the time. Like others who have posted on this thread, I found the book complex, full of too many characters and stories. Often, I felt like I was reading a history textbook, sometimes skimming through the most difficult parts. But as soon I was ready to give up on The Silmarillion, I would find a chapter that intrigued me. Such examples were the stories of Turin, and Beren and Luthien. Such chapters were what drove me to the end. And though I finished The Silmarillion still puzzled by much of its content, ultimately I was glad I read it. While some of the book was confusing, I still learned a lot and understood Middle-earth in ways I hadn't before.
Almost four years later, and I'm thinking it's about time I re-read The Silmarillion. After all, over the years I've seemed to forgotten much of its content. Even the story of Turin has grown cloudy for me.
Besides I found through my experiences of re-reading LotR, that reading a book a second time can truly help one to understand it better. After re-reading The Silmarillion, perhaps I'll even start on HoME. I've owned the first book for years, yet it has remained untouched, save for when I took it with me to college. (Then my perfectly conditioned book became partially ruined from water damage due to the poor handling of my checked luggage- that happened three months ago and I'm still bitter about it. Anyways, that experience is a long story and I won't get into it....)