I've been considering the cases of Singapore and Hong Kong, two cities which share a lot of historical and current similarities.
After the Second World War, the British resumed rule over Singapore, but with self-government and independence as eventual objectives. This culminated in Singapore's independence from the British Empire and failed merged with Malaysia in 1963.
On the other hand, while the post-war period in Hong Kong brought democratic reforms and economic development, there seems to have been no talk of self-government and/or independence.
Does anyone know why this might have been the case? What were the major difference between the two cities that lead to Hong Kong staying British until the 1990s?
So unfortunately there were no opinions on this question. However, I did learn about the Young Plan (1946) that was aimed at introducing representative democracy to Hong Kong after it was recovered from the Japanese.
The plan called for a directly elected municipal council that would handle some matters of internal administration. It also provided for limited presentation of locals in the legislative council through the election of two 'unofficial members' of the council.
The plan was never implemented for two reasons:
The legislative council didn't want to transfer power to the new municipal council.
The plan was drawn up by HK governor Mark Young, but he was succeeded by Alexander Grantham in 1947 who opposed the plan and didn't make any attempts to implement it.
Perhaps in an alternate timeline where the Young Plan were implemented, Hong Kong may have gained independence. However, given that the Chinese Civil War was settled by 1950, it would have probably gone the same way as OTL, just with a few more decades of democracy before the handover to China.