Chee won't. Singapore has been in the longest bull run in history, from the early 1960s till today, with minor speed bumps like some recessions here and there. But the trend is still a continued bull run. As long as that is maintained, Chee will remain a loser.
The conservatives and labour parties take turns to win elections because neither party can sustain the country's success long enough to cement their grip on power. They do well for a few years, then mess things up big time and the opposition party wins, and the cycle repeats itself.
Singapore is different. It is a story of success for nearly 60 consecutive years under a single party that has improved Singapore from year to year. Chee will have no chance as majority of the voters don't want to rock the boat.
I agree, what you mentioned about a two-party system works for them. Because both parties have almost equal strengths and weaknesses.
And yes, Singapore is different. Because we only have one party. The founding fathers of the PAP saw to it that we have one party for as long as possible. So, even when things go horribly wrong for the country due to PAP policies (overpopulation, wide income gap, high ministerial salaries, etc, etc), there was no party strong enough to challenge them. Only a stunted token opposition, Hong Lim "protests", powerless bloggers.
Don't want to rock the boat? Bullcrap, the boat is already sinking. The bull run was over a decade or so ago.