The younger generation is more educated but not necessarily more politically aware. The education system has indeed served its political masters well, churning out technically skilled people but not people who are aware of their political situation.
I dare say even those in Arts courses suffer from this syndrome. Know everything about the world but somehow blind to their own backyards.
WP has benefitted because its leadership recognized years ago that to win the race you must start from the ground up, working through the heartlands and getting around all the obstacles that the media will place in front of you.
I think no one in the opposition camp has ever been under the delusion that SG is a true democracy. At least, no one credible has ever believed that. The methods must be those relevant to the situation. No use banging your head on a block of iron, thinking your skull can match its strength.
It is basic politics that the canvassing starts at the heartland level. True not only in SG but in all 1st world developed countries too. The only diff is SG is not a 1st world society yet and the playing ground is unfair. A real opposition navigates this minefield with intelligence and political astuteness.