I recently had some short PM discussions with Repatriate regarding Taiwan. Since he’s an American with Taiwanese parents, he’s a type of "Taiwan insider" with an American perspective, similar to Momopi and Winston. His background contrasts sharply with my own and other LT western expats in Taiwan. Below is some historical and cultural context to OP as expressed through his insights in these PMs. He gave me permission to post them.
Rock Some people just perceive everything Chinese people do in a bad light. They are seen by some as being selfish, rude, greedy, stingy, etc. The American friend I mentioned is a sensitive Jewish guy, on the short side, speaks Chinese, and had done decently with local women in spite of being just average looking. He gets annoyed by the way taxis drive, people bump into to him and don't say excuse me, the loud noises, service at restaurants, etc. He's generally not done well in the office politics arena at the jobs he's had too. Thing is, he's pretty direct and rude himself. Sometimes he will lecture waitresses or other employees on how to do their job, etc. I even remember him once walking into a public restroom at a hotel, noticing a couple Taiwanese guys smoking, and telling them loudly and directly, "you're not allowed to smoke in here!" like he owned the place. He's really lucky not to have ever been beaten down given his attitude and behavior.
From my POV, his perception is off-kilter. When Taiwan people bump into to me, the most common response is a "sorry" in accented English. Service quality varies according to venue, etc. But generally, with some exceptions, there is a sincere attitude to make customer happy and correct any problems even though there is no tip on the line. Most taxis drive as best they can given the high traffic density. And cars will usually stop to avoid hitting pedestrians, quite different than places like DR.
Repatriate It could be a case where someone comes from a background that is very similar to Chinese people in many ways and so that triggers some internal self loathing mechanism. Then again some people often develop a superiority complex when they go abroad. I have no idea if that was what his problem was but local people do tend to home in on poor attitudes. It's harder to disguise because people are always watching you as the foreigner. If this is the same guy that likes Thailand more it could be that Thais give off the perception of being outwardly friendly and passive. However, if he treatd Thais like that regularly he isn't just risking a beat down but getting sent to the hospital with permanent injuries or outright murdered.
Rock Are Taiwanese selfish? That's a relative questions cus humans are born with a lot of selfish instincts. But I can cite ways in which an average Taiwanese would probably be considered less selfish than an American. For example, who is more likely to make major personal sacrifices or life adjustments to please their parents or family members. Who is more likely to go with the flow in school or at work in order to foster group harmony? Where is it more common to stick with general norms so as not to stand-out or disturb? Where is it more common to stick with general norms so as not to stand-out or disturb? As for rudeness, I think Taipei has become pretty polite in general - part of it is good education, part business motivated competition in service businesses, and perhaps you can throw in the effect of some Japanese and western influence. It used to be common at queues in banks and other institutions for people to swarm the front or have older women cut in front of you. That behavior has been markedly reduced through awareness and education. Anyway, most places now use a number calling system.
Repatriate Taiwan's modern history probably has a lot to do with this emphasis on social harmony and reserved personalities. I talked with my parents many times about what Taiwan was like back in the 50's-60's. My mother said that Taiwan in the 60's was pretty ugly, there were gangs of disaffected youth everywhere, government restrictions on rights, and unemployment was very high. It was also during this time that the civil govt would conduct secret purges. People generally lowered their heads and tried to avoid being on the radar. Standing out too much socially (especially politically) was frowned upon. There are several Taiwanese films about this period which talks about the general moral and economic decay in Taiwan, TW was probably much more similar to Southeast Asia during this period. City of Sadness, Dust in the Wind, A Brighter Summer Day are all good movies depicting this era. People were actually afraid the country might not survive and there was a feeling of desperation and transience with the KMT families who were integrating into this new society.
Then when the 70's-80's rolled around economic reform started to become the big thing. The late 70's-80's was a time of high prosperity for Taiwan and people became more intensely focused on economic matters. Academics, family, and rather conservative practical living became the emphasis. The TW traits that Winston always complains about probably became the bedrock foundation of society around this time. There was a sense of purpose and the risk taking, rebellious, and indolent attitudes of the 50'-60's just weren't the norm anymore.
Rock Consider one more scenario - a bunch of youths in a NYC subway car vs. a Taipei MRT car. In NYC, I've seen all kinds of rude and selfish behavior - kids do acrobatics or loud performances and then busk for tips, eat and leave their trash on the seats, talk extremely loud and aggressively, fight, or even attack people. I've only spent a few months in total in NYC, a relatively safe US city, yet I've seen all that stuff go down. Some of it is rather commonplace. I also saw someone get stabbed during the morning right in Manhattan Chinatown. Now consider Taipei. I've spent years there and frequently ride the MRT and bus system. Its kept spic-and-span clean. People totally respect all the rules. Worst thing I've ever seen is a few students getting a bit loud, but just slightly. Guess what happened? A middle aged women told them in a polite way to pipe-down so they hushed immediately and even looked a bit embarrassed. I almost never see any kind of violence in Taipei and have never been any kind of a crime or verbal assualt victim. On average, if you behave properly at least, you are much more likely to encounter threatening behavior living in NYC than in Taipei; kinda like comparing the chances of seeing a gator in Florida vs. Minnesota. The difference is material to say the least. So is US society really less rude and selfish than Taiwan's?
Repatriate Well authors like Mark Twain, Hunter S. Thompson, Matt Taibbi, Noam Chomsky, etc.. who have particular insightful commentaries about American culture have always pointed out that there's definitely a mean streak there. I doubt that's unique to America though but since America is still a "young" country in many ways maybe the traits that we call selfish are more pronounced. Social harmony matters less in America unless it has to do with practical concerns. Matter of fact to some extent America thrives on social disharmony. Competitive aggressiveness, assertiveness, individual worth, etc.. are all valued by the U.S. I'd say relatively speaking on an interpersonal level American culture is definitely more outwardly rude and selfish however the reasons why are complex. Maybe it's the natural state of things when you have large groups of culturally dissimilar people living together for decades who are brought up in a culture of competition and individualism.
In some ways America is (was) also the ultimate meritocracy. If you're willing to be selfish, rude, but are also competent, ambitious, and competitive you can go very far. I think this type of person would encounter many more roadblocks in a country like Taiwan where harmony and a certain degree of social finesse is required.
I suppose this is changing slowly though in a rather negative way in that America isn't as much about pragmatism these days as it is about maintaining a certain status quo and instituting a class system.
Rock Its funny that in spite of Winston's ancestry, it gets passed-over as a potential HA destination by most of the forum members. Its also pretty much off the map in general as far as guys looking for Asian women are concerned. I suppose that's a good thing. Cus if foreign guys flocked over there like they do to Thailand and PI, it would get damaged badly. When a minority group is small and low-key, they are generally not perceived as much of threat or annoyance by the locals. But once they reach a visible critical mass, all the hate starts to come-out, especially if a significant number affront local sensibilities.
Repatriate I think it's pretty much impossible for Taiwan to support a big market for foreign men looking for LT partners. I guess it's just the way TW culture is. You're right, if it became an internationally famous (or infamous) place for this or associated with p4p then the doors would slam shut really fast.
Once upon a time Taiwan hosted a U.S. military base around the Vietnam war. When various SEA and NEA countries sprouted red light districts and heavy P4P type presence the Taiwan population didn't fully embrace that sort of sexual permissiveness. It was considered very taboo and low class that's why you don't see a substantial number of war era hapa children in Taiwan that you see in SE Asia or even in Korea.
However, with that being said TW is definitely a destination already for Japanese men to marry TW women. That's the #1 pairing by far for TW women, there's at least twice as many TW women marrying Japanese men than any other foreign nationality. There are a few famous half Japanese/Taiwanese actors out there..one notable one is Takeshi Kaneshiro
http://en.wikipedia.org/wiki/Takeshi_Kaneshiro.
- so no time to write till now. 
That's the first time I ever encountered that much bad attitude in Asia for no apparent reason.