Money is not the problem with immigrants who really want to leave. It never has been. Poor people with no money have successfully emigrated to countries like US, Canada, etc. All very desirable countries. The mental attitude and toughness is everything. Unfortunately, sinkies have a kiasu mentality and have been too closeted in singapore to take the chance. they are afraid of everything. People from other countries do first and worry about it later. People in singapore worry about it first and never end up doing it.
I can guarantee you that the fear of losing money on the sale of a flat or repurchase of a flat in the event they come back to singapore is more of a mental fear then a monetary fear. A small percentage of singaporeans I have known simply gave up their citizenships, took their CPF out, sold their flats and cars and left. One opened a small grocery store in a small town near the Welsh border in the UK. This forced him to change his mindset completely and forced him to succeed in his new country, for the simple reason that he has burnt all his bridges and there is no going back. Usually the people who do this will land in their new country with six figures in their pockets to buy a much cheaper house and car and still have reserves. As well, they can speak english and have a good education thanks to the singapore education system. With so many advantages like this, you must be an idiot not to succeed.
The vast majority want to keep their sinkie passport "just in case" and always have this crutch to lean on if times get tough, so they can run back to singapore. But this means they don't put in their max effort to succeed. They are not willing to clean toilets or wash dishes. I look at my late friend Wilfred Skinner, the former Singapore National Goal keeper. He took a very bold move that many people could not understand at that time. He was a somebody in singapore. People know who he was and he was an assistant superindent in the SPF. Its a good job and he hobnob with leaders and celebrities. He gave everything up to move to Vancouver. He was nobody in vancouver. Just doing some small renovations jobs like putting in a new a bathroom for some one as a contractor. he never intended to come back to singapore. he was willing to take all these jobs and succeed. In fact, I had to go to vancouver to see him, as he hardly bothered to come back. he did not make a lot of money, but i never saw him so happy and contended. he made enough to buy a house, which by now must be worth over a million $ if it still remained with is family. He never once had the attitude that he can always go back to singapore if it did not work out in canada. he is one of the few sinkies that openly told everyone he is leaving, including sports minister EW barker at that time. Unlike most sinkies who sneak out in the middle of night and never told anyone. If sinkies have this kind of attitude, they will never come back to singapore, regardless of how much they lose, and make sure they succeed there.