1995 and 1997 were not that long ago, though I recognize that for some contributors here that's more than their lifetime. And they fell but one win short in 2007.
Those seasons came following a decades-long epoch of incompetence (which at least gave us one hilarious movie, Major League). It hasn't nearly been so awful in recent years for Cleveland fans.
Yes, they'll be back someday. Be careful what you wish for -- making it to the Series and winning it are two different things, and Cubs fans, bless 'em, keep making this mistake.
Yes, but it could take a either a really long time or really short time. They seem to be at a turning point in their franchise history after being good for several seasons with Lee, Sabathia, and Sizemore, and they need to make some strong managerial and business decisions to take a turn for the better. They need to find some good, young bats and some quality pitchers to at least be competitive. If not, they could turn out like the Royals have for years. If so, they could rise from the dust of mediocracy to the World Series like the Rangers did.