Taiwan Explorer (formerly My Kafkaesque Life) has an interesting and more-thoughtful-than-most post on the downsides of living in Taiwan.
My reaction to it is long enough that I think it deserves its own post here, but definitely go read his thoughts first!
1.) You will always be a 'waiguoren'
Yes and no. Yes, in that the vast, vast, vast majority of people you meet will always think of you as "NOT US", or someone different, and there's nothing you can do about that. Taiwan Explorer covered that part well.
But there are inroads you can make. While most local friends you make here will think of you as their "foreign friend" or otherwise think of you as "other" (to the point where they might exclude you from gatherings that there is no reason to exclude you from, or just forget), it is possible to make friends and connections who just treat you like a person and local vs. foreign doesn't come into it. It is definitely possible.
And you will meet people who - if you speak the language(s) and are well-integrated (or are trying to be), will say "eh, you're Taiwanese!" or "you really should have the right to be a citizen and vote here, it's not right, you're as Taiwanese as me". While some are joking or giving empty compliments, I do think some of them mean it.
Frankly, most countries have cultures were outsiders will always be outsiders - I joked once while visiting Brendan in Maine that if we were in a horrible accident the headline would read "Long-time Maine Resident and His Non-Maine Wife in Accident: Real Mainers on the Scene Recount the Tale"! So it's nothing new or surprising.
2.) You will have to live with stereotypes.
Yep. But you can also make friends who see past them. And stereotypes aren't anything new either - certainly I've heard my fair share of them growing up, even in the People's Republic of New York.
Also, I find that inward "island mentality" is only true of some people (and honestly, in the US I often encounter the opposite - being cocooned within a large country makes some people inward and ethnocentric - they're so far away from any other country or group that they start to turn in on themselves. I blame the whole hackneyed bullshit notion of "American exceptionalism" on just this phenomenon). For others I feel that the fact that Taiwan is a small island surrounded by other countries and deeply affected by them has made some people aggressively outward-looking. I've met many extraordinarily worldly people in Taipei, including many of my students. Most people are normal - somewhere in the middle. Like we all are.
Not much to say about #3 - although most people I know do know something about Taiwan - they just know the wrong things - "well I read that Chiang Kai-shek was a good man who saved Chinese culture by bringing it to Taiwan and then did great things for Taiwan like developing it" said one relative. Yeaaaaaahhhhhhhhhh noooooooooo. Same for #4 (yep) and #5 (yep - although it is possible to become highly fluent). I do have something to say about #6 but will post it below.
I agree about Taiwanese food. But as for good Western food, I actually think the selection is okay. Not amazing, but okay. I can get good bread (there's a place near us with great baguettes), cheese, I get goat milk delivered, and Taipei is dotted with great coffeeshops. I'm actually quite alright with the Western food situation. Whatever I can't buy I can cook myself, too.
Nothing to say about #8 and #9 - yep.
10.) Population density
Yeah, but I see it as a positive. I like living this way, near other people, near lots of things. I like that everything is so close together, which is only possible with high population densities. I'd probably feel right at home living long-term in New York City.
I also don't think it's hard to find an affordable, spacious apartment in a quiet neighborhood. We have 30 pings - 3 bedrooms, a generous living room and a Japanese tatami tea room (albeit a very narrow back room and galley kitchen). We have a dryer, a bathtub and "wood" (high quality restaurant-grade plasti-wood) floors! Outside most of our windows is a courtyard/playground/public space. We're on a busy lane but we can't hear much, if any, traffic. Sometimes we hear our neighbors but nothing too annoying. We're right in the middle of downtown Taipei, in Da'an district, and we find our rent to be quite reasonable (maybe NT25,000/month isn't reasonable to some, but for a couple, in Da'an, near the MRT, three bedrooms, we think it's great. Everyone always asks me my rent anyway, it's not a personal question in Taiwan so I may as well spill).
And it's quiet, affordable (for us - I know not everyone considers our rent 'affordable') and central. So, hey, it is possible to do just fine with apartments. I will stay here as long as possible. You will pull me out of real estate heaven only after rigor mortis sets in, and not before.
Adding some of my own:
11.) Taiwan seems to have multiple personalities vis-a-vis sexism and gender relations
I just don't know what to think. On one hand, a woman was nearly elected president here without much problem at all, or even commentary, regarding her gender. Truly, nobody seemed to care. The most beloved mayor in Taiwan is a woman, and while some people make fun of her hair, nobody disparages her gender the way Americans do Hillary Clinton (or Elizabeth Warren for that matter). In all of Asia, this is probably the best place for women.
It's easier for women in Taiwan to hold good jobs, have great careers and have positions of power. The whole "men don't want a female managing them" doesn't seem to be much of a problem here judging from the number of female directors, CFOs, COOs, partners, senior physicians and department heads I've met. Taiwanese women basically run finance and accounting. An average Taiwanese woman is almost certainly better off in terms of opportunities than an average woman of any other nationality in Asia.
Men in Taiwan seem to be catching up to this whole womens-equality thing faster than their counterparts in China, Japan, Korea or the rest of Asia, and this is one country where I can go wherever I want, whenever I want without fearing sexual assault. I can't say that for America.
On the other hand, there are so many ridiculous notions that I come across regarding women: that we're "more interested in fashion than politics", that we are "less adventurous" (I was really offended when someone I knew gave that as a reason why there were fewer female expats in Asia), that we always, across the board, like pink, that we do most of the housework and child-rearing because we're "good at it", or other sexist practices allowed to continue because it's "culture" (NO, IT'S JUST SEXISM).
Jump-you-in-the-street rape may be unheard of but marital rape is frighteningly common and unreported.
I've definitely come across a lot of lookist-sexism (the idea that a woman's most important feature is her looks, not anything else she might have to offer, and that pretty women are automatically worth more than any other women) and momma-sexism (the idea that of course every woman wants to have a baby, that of course they will be better at raising it because women just are, that it's unnatural to not want to have children) and marriage-sexism (the idea that all women want to get married, that all women act a certain way especially in relationships, and that they are fundamentally different from men in how they act). Also acting-sexism (men can drink and swear, women are ladies who don't drink a lot, or at all, and never swear because that's not ladylike).
There is still an entrenched 'mistress' and 'hostess bar' (and prostitute) culture, which does have tendrils in the business world, making it hard for women to rise to positions of power in some fields. I've met otherwise progressive guys refer to attractive female employees at their company by their employee numbers, like they're livestock (NOT COOL), and there are a lot of sexist beliefs among the older generation.
Add to that the current government's total lack of interest in progressing the cause of gender egalitarianism, the lack of readily available and affordable oral contraceptives to poor women, and the lack of no-fault divorce or solid legal precedent for handling child custody or domestic abuse cases fairly (or divorce petitions for that matter), and things are not entirely rosy.
So I just don't know what to think. America's pretty fucked up too in this way - most places are. And Taiwan's better than most, but still not good enough.
You could spend a day talking to young progressives who have wonderful, egalitarian, mutually respectful relationships and family units and who aren't threatened by women and think things are great. Then you could have to listen to your sexist-as-fuck boss (scratch that - former boss!) blab on about "a man's mind is an ocean and a woman's is a river" or some bullshit and think things are terrible - it's enough to give you whiplash!
Either way, if you're a woman living long-term in Taiwan, you definitely have to face this. It's not so much that it's different from the West (which is far from perfect), it's just that it's expressed along such different parameters. In the USA there were legal protections against a sexist boss, but you had to watch your back on the street. Here, you can walk freely, but your boss is just as free to be a misogynist dick.
12.) You have to get used to people being overly direct in unfamilar ways.
I actually don't agree that Taiwanese culture is generally an "indirect" one (Taiwan Explorer's #6). Communication can be indirect in ways that may be unfamiliar to Westerners - such as showing anger, disagreeing or confronting mistakes (in some ways the cultural difference here might come off as passive-aggressive to some Westerners, and yes, I still struggle with this. I actually have the same problem with West Coast Americans). But in other ways it's actually too direct! "What's wrong with your face?" if you're breaking out, "Why don't you want to have kids? You should have kids!" after you've answered a question honestly (OK, my family does that too and I hate it), "You've gained weight!", "Well even though you don't have a beautiful face you are pretty smart, maybe someone will like you" and so on.
Yeah. You just get used to it.