They probably downloaded his programming to Goh Chok Tong since they worked together for a long time. : ) So, there succession system has a lot of stability. I am not versed in political economy to say that their system will lead to it's own decline.
But, the income disparity can probably be fixed by simple social engineering which they have a lot of flexibility of doing. Don't they have a social safety net better than our American SS?
My impression was that old lady who cleaned the lavatory for dime tips drove off in a Benz at the end of the day.
Yes, they have the CPF to which both employer and employee contribute a percentage of monthly salary. With the benefits of long term compounding, it is really great for retirement.
Also the government developed housing adds to individual wealth with appreciation in value. I once met a taxi driver who was planning to emigrate to Australia where he felt life was more laid back than Singapore. In chatting with him, he revealed that he was worth more than a million Singapore dollars. I asked how, and he said his HDB apartment was worth >700K and his wife had a good job so had about 500K in CPF which they could withdraw early if leaving Singapore permanently. He was probably in his mid 40s so not bad going for a taxi driver.