How in the world would you get a maid for <$2k / month in Singapore, Japan, Taipei and South Korea? I know Japan personally - it's more expensive to live in major Japanese cities than it is American cities.
I have this problem with the California mentality as well. I've traveled extensively within the US (as well as outside), and most major cities are pretty much similar to me. Even with the 2 million resident city I was in with >80% people being Caucasians, I had no problem finding major stores for necessity; food choices weren't nearly as abundant as CA but there were a few good options around. I'm with you in regards to retiring outside of the US, but wouldn't bank on having a live-in maid. Countries where you can actually afford a live-in maid typically don't have nearly as good of a health care system, and around retirement age is when you start to have problems; countries with health care where you can depend on typically are nearly as costly or more than the US. I could see myself living in, say, Southeast Asia for a few years but would be cautious as I approach 70. I simply don't trust hospitals there.
My ideal retirement would be living elsewhere for half a year, rent out my home for that half (AirBnB or something of the sort) and living here for a half a year. With air travel so easy these days, there's no need to confine one's self to a particular location. You can give me a house overlooking the beach in San Diego, and I still would want to travel to get out. However, there are people who don't have such travel yearnings, would rather have a small house, lower QOL, to live in good weather/close to friends, and that mentality is valid too. To each his/her own.