Kaohsiung

Great city in Southern Taiwan on a major port.
Lots of stuff to do if you like the outdoors. A mountain to climb, a beach to go to, and trains and buses readily available to go to surrounding outdoor activities.
Cons:
English speaking is not great, but the locals are. And even if you don't speak Mandarin they will do their best to help you. Plenty of English speaking doctors, dentists etc. Most restaurants have a double menu. So it's not that big of a con and there are many classes that will help you learn at least the basics.

Pollution and Air Quality are terrible, not so bad that you can't go out and can't function, but the south is home to lots of refineries and factories that pay their way out of keeping up to standards and the air from China blows right over the western part of the Island compacted by a mountain range from the central to eastern part of the Island so no where for the bad air to escape too. Lived in Kaohsiung 3 different times for a year each time and it is not unbearable if you don't have any breathing or allergy conditions.

Scooters/ Also a Pro? There is a very clean efficient Metro but lines are lacking making it hard to get out to the neighborhoods that don't have easy access (Eastern Kaohsiung). The government is cracking down on crappy old polluting scooters, but that doesn't really help the people that like to drive on sidewalks and such.

Traffic Laws and signals ignored - The government has installed cameras and over the years things have gotten better, but the lack of regard for traffic laws does make driving and walking dangerous. It's probably the biggest flaw within the control of the local people and government. There are hardly any sidewalks (especially in the older neighborhoods) so it does make you keep up your alertness while walking or biking around town.

Pros:
Aside from the traffic wildness, the whole country is extremely safe and most people are honest. Women are safe, children are safe, elderly people are safe. As a young woman never felt unsafe. Can walk anywhere at 3 am. If not for the pollution this is where I would want to raise a family.

Parks- Lots of parks in the city, lots of things to do and see in them.

Museums- Lots of museums and everything is in English in all of the major ones. Great for children and school trips.

Community- Not just with all the Expats, Nomads, English teachers, but also friends with many locals. It's easy to make friends if you take the time. Join sports leagues, dance classes, jiu-jitsu classes, art classes you'll make plenty of friends and the local friends will help you to experience the actual culture of Taiwan, which is worth coming for. It also helps with learning the language to get over a bit of the culture shock of being illiterate. Of Europe, The American, (have yet been to Africa), this was culturally the coolest and most interesting of all of the places I've been. Just so much history and culture on this tiny Island.

Culture - Maternal Culture, I use to threaten kids by calling the head of the family, aka Grandma. Aboriginal, Portuguese, Japanese, Chinese, and US all wrapped into one tiny place. Festivals year-round.

Food - Excellent, even for picky eaters, but better if you're adventurous. Cheap food that's great, Western restaurants while more expensive are still really good and comparable to prices overseas, it's not crazy expensive.

Costco locations and carrefour so you have access to most of the goods you can get at home in Canada, Australia the US or Western Europe.

Affordable 2 bedrooms, new, non-luxury around 17,000NTD. Luxury New around 24,000NTD, older not luxury less than 12000NTD.

Wifi and Technology in general - Great Wifi, Great prices on Computers and tech stuff. Even a whole street dedicated to selling and fixing computers in a central location.

Cafe's - Lots of cafes with wifi, free wifi mostly everywhere though. Coffee culture was hardly there 12 years ago, it's a relatively new concept, but it's growing exponentially, check out SPR coffee.

Healthcare - Great and reasonably priced. Have been in accidents and have been injured playing sports. Even if you aren't on the national health care, healthcare is easy to get and affordable, minimal fees. A serious accident/injury/illness would require some insurance though so check into that when you get here.

Some miscellaneous stuff:

Nightlife is so-so, Not many nightclubs, but the ones that do exist are okay and you'll find it hard to leave before daybreak. At which point you'll be able to hit up a breakfast shop before going home to pass out til noon (life as a young English teacher, or sometimes a major social event in which every English speaking local and Expat/foreign student shows up)

The weather is hot most of the year. Summer is brutally hot, but fall and spring are nice if you like around 26 or so. Winter is nice, but it can get cold, there is no heat in the apartments. By cold I mean the occassional string where the temperatures dip to around 10 or so. sometimes cooler. Doesn't last long, but does happen. You can buy heaters almost anywhere if you need them.

It is really easy to get around Taiwan, via buses and trains. Busy during holidays so keep that into consideration. They are also very affordable. There is so much to do. Mountains, Festivals all the time year-round, Kenting(south), Taroko Gorge(northeast), The eastern side of the island is gorgeous and less populated. Air Quality is much better on the other side of the mountains. If you're a city mouse and you like getting out, Taiwan is a great place to be.

Bureaucracy exists for visas and other life stuff, but given the language barrier, doing this kind of stuff in Taiwan is substantially easier than even being a citizen and the bureaucratic crap we put up with in western countries, especially Europe and visa processes. A dream compared to the American/Canadian processes. Most of the people that stay here for a long period of time and get their APRC(permanent residents) will tell you it's because life here is easy. And it is, if you make a certain threshold 2000 USD you'll live like a king or queen.

Kaohsiung is a more relaxed city as compared to other major cities in Asia. You can enjoying working and taking vacation in this warm city. However, it is not quiet a English speak city. So, it is better if you know some simple Chinese here. It also close to Kenting, a beautiful beach area in Taiwan. Good place for remote working and vacation.

Lovely city, nice people, easy to get around and great warm weather.
Kaohsiung is a fantastic hub for expats and nomads, however, the nightlife here can be a bit dull.
Still though, great fun all around, and very cheap and affordable.

An amazing city for the value. Beach, MRT, Sun, and about half price of what you would pay in Taipei. Also, lots of super cheap flights all around Asia from the city airport. Been here a year so far and I like it. Not much in terms of night life, but a good digital nomad community. Also, really helps if you speak Chinese. An undiscovered Gem that I could see getting more popular with digital nomads in the next few years.

The City and the area is quite nice but its very sleepy city... There is not much cultural stuff going on and nightlife is shitty. I got bored fast and mooved to another city