If you find yourself in a situation ala the Toronto Maple Leafs (mediocrity accross the board, foregone picks, wasted picks, underserving contracts) then you're basically relying on the sport- watching impulses of the masses who will still pay to watch a bad product. The Raptors don't have a strong enough brand I think to overcome another 10 year stretch of mediocrity/crappiness.
Its a superstar league with too many teams and not enough great players. I don't believe in relying on the draft as the only measure for success, but, it appears that there are at least one or two potential superstars who will be entering the NBA the following year and I say we go for it.
An Andrew Wiggins in Toronto would be like Rose in Chicago: an era of greatness.