I automatically went into the dark age from around 1999, I was 12 at that time, it might mainly because I had other interests, and many sad things happened to me in my teen age, therefore LEGO was not in my mind, personally I think the design of the sets in those years were not so good, they just can't attract me. I bought less than 5 sets between the period of 98-2007 .
Just until the year 2007, I spotted a 7654 in a sale inside a store, and then I went to the web and search through auction site, eventually bought a 7655, the dark age has ended, and I am on it again. During 2008, I bought back a lot of old star wars sets, actually some of the were very expensive, If I could start it one or two years earlier, then I can save a lot.
I think the LEGO has been improved since around 04, there are a lot of new minifigs heads and hair, and movie themes, the playability increased much.