Taiwan isn’t NEARLY as cold as New England or the Mid-Atlantic. I think it has snowed in Taipei city once or twice in the last 10 years, and the snow was so thin you had to look for it! So I don’t think that will be an issue. But nor is it a tropical island, This is a sub-tropical zone, so there are real temperature changes season to season, fall being the most comfortable.
Pace of life: Taipei is perhaps the fastest paced place I’ve lived in. Well, I suppose it has slowed down a bit, since traffic is less crazy than it used to be. But this is no slow-paced lounge about on the beach island! You can certainly find that if you want it, especially down south, but by and large, I’d say it’s a fairly industrious place, which accounts for its rapid economic development and urban change. Taipei changes constantly (mostly for the better, IMO).
At the end of the day, Asia being Asia, and ALL foreigners having adjustment issues, I think you might base your decision on where to go less on the race issue and more on, well, where your heart takes you. You already have an “in” with the Taiwan temple experience, and that ain’t nothin’ to shake a stick at. You’ll find that experience will endear you to more than a few locals, since religion is important to many people here. It’s not the “wear it on your sleeve” variety that you find in America, but it does have an important place in many people’s lives.
Also, be wary of blanket statements made about Taiwan, Japan, or Korea. These are all very complex places, all of which are changing at a breakneck pace. Examples:
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I’ve been to Japan 6 or 7 times. The last time, just a few weeks ago, I noticed a much larger number of people actively speaking to me in English. This isn’t anecdotal or coincidental, since I go to many of the same shops every trip. That’s actually a good sign, since in the past, it was hard to coax people into speaking English.
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Korea (well Seoul, at least) has become quite a cosmopolitan place. I went back last year for the first time in 5 or 6 years. There are a lot of decent international restaurants. I find the people there quite friendly The subway system is excellent as well.
So, at the end of the day, anywhere in Asia will be what YOU make it. That means have an open mind and a good attitude. My first impression is you already do (which is why I’m spending so much time replying! 
) so you’re on the right track. As you know, having lived in P.R., NYC, VA, etc, a place can be anything to you, and your mental filter and way of seeing things will largely determine your experience. That is why you’ll find White folks who love Taiwan, and those who are miserable. You’ll find Black folks who stop thinking about race (like Miltownkid. I remember a lot of our earlier conversations were about race. Then they drifted to other things like Linux and sending photos over cell phones. 
) and you’ll find Black folks who can’t stop talking about race.
Another important thing here is having a good network of friends. Again, you’ve got a leg up through this site. See if any of your temple friends can introduce you to people in Taiwan. (Get their names and cell phone numbers.)
Work: I don’t think this will be a big problem. I like your idea of looking around the island first, though. That’s much better than coming here and frantically looking for a job. Oh, but I’m somewhat concerned about your wanting to make “a lot” of money. The cost of living here is lower than in the US, but I think English teachers make around $1,700-$2,300 a month. Not too sure - maybe someone can verify that.
Language issues - critical in learning about a place and learning to love it. You’ve got mad linguistic skillz (always wanted to say that!), and you’re already learning Mandarin.
Heck, what am I saying? Taiwan NEEDS more high class foreigners like you! Got any brothers or sisters? Send em over! 
LMAO!!!
) that it might be too strict and stiff for me.