As another poster stated, the execution of the "relevant" ideas put forth by the filmmaker was likely RB's major problem. I think it's partly that (the characters are caricatures - Troy's the Rebel, Janeane Harafolo is the slut who's omlynthat way cuz she fears commitment - nobody really resembles a real person except, possibly, Leilana. Also, the timing of the film wasn't great - "Alt" culture, or Slacker Culture - whatever you want to call it - was kinda burning out/winding down, and a film like RB, which wants to be a Generation-defining (or at least -Capturing) work, missed its moment, I think.
What you state about Leilana and Troy wanting "everything handed" to them is basically a misunderstanding of the times/chaccters, IMO. It felt to me that young people at the time didn't really want anything at all. Maybe I misunderstood it as well, but one of the things I found so refreshing about that time was that Slacker-culture was a major influence, people seemed to want to believe in truly alternate lifestyles. Thy didn't want "Jobs" or "Careers". Think about how the major bands of the time shunned - or wanted to seem like they were shunning - "stardom". Apparently it was all a pose because it disappeared as quick as it bloomed, and by 1996 it seemed it was business as usual. Not unlike how the hippie movement became money-worshipping yuppies, but not as huge.