At the risk of being a spoilsport, my respond was NO. The reason is because Aljunied GRC, if it were to be lost, was after all a low hanging fruit. Just winning that don't a watershed make!
Now if the opposition were to win against Lee Kuan Yew's Tanjong Pagar GRC and nothing else that would be a watershed moment. If that were to happen it would really signal that the feeling on the ground had indeed shifted. Defeating the old man would be both sweeter and more profound than winning any other "low hanging fruits" GRCs. Hey even if the opposition did not win in the old man's GRC merely win with a respectable score say 30%, it would be a watershed moment! For a man who demand perfection that would be a real stain in his record if not his ego. Something he'll never be able to live down.
The repudiation of Lee Kuan Yew would also have a practical impact far beyond that impact of having oppositions in Parliament. That is not to say having oppositions in Parliament is not a good thing. Such an event would certainly give any reformist -- i.e. those who are not together with PAP current policies -- elements to raise. It would also free the nation of being so beholden to the old man and what he stood for, and move on. Alas this is not going to happen and an opportunity lost most probably forever. I can't see the old man contesting the next election after this.
Nevertheless, I wish to point out that should the opposition win one or two GRCs, I believe it is just reward for member of the oppositions who have fought so hard and given so much to the nation. Even if a clean sweep were to achieved by the PAP, the oppositions in my heart have already won and in time to come will win. Such a result however would reflect on the sad state of the electorate themselves!
