I'm several years into my "1-year experiment" that was living outside of my home country. This was suggested to me by a friend when I wasn't really happy with my employment options after graduating from college and he suggested that I go seek out an overseas place to live for a year and see if that helps you to understand what you want to do with your life. Well, it did in a way, but mostly it just made me want to not live in the country that is on my passport.
There are a lot of benefits to living this way but it isn't all sunshine and rainbows. Here are the downsides that come to mind.
Always having visa issues
I am sure that this is something that is a problem in other countries as well but in Thailand, this is something that is omnipresent with the expat community. No matter how legitimate the person in question is, there are always problems with immigration. I maintain a teaching job that I do not like and only have a bout 10 contact hours per week simply because they have an HR department of sorts that handles all the ever-changing rules as far as my visa and work permit are concerned.
I am able to "get away with this" because I have been consistent and reliable for this school. I don't think it is a secret that I don't like working there and it is not a great job. However, the English positions in this school have become a revolving door of sorts and almost all new teachers break their contracts and just do a runner, leaving without telling anyone and then the classes they were meant to teach just don't have a teacher anymore. I have tried telling the school that they could fix this if they just improved the conditions that we work in but I don't think the admin actually cares. They get a certain amount of money in grants and that money continues to come regardless of who is working there.
I suppose I could talk about that at great length but in a shell, I only have this job in order to keep the visa-vultures at bay - The salary is a joke and I loathe going in there.
Other people I know are on retirement visas which require putting a certain amount of money in a bank account and leaving it there. Even if they are totally playing but the rules, they are constantly hassled by immigration when they go and renew their visas. People on "student visas" probably suffer the worst treatment and with good reason: Everyone knows that these people are not actually students and they simply pay money to a school to run cover for them. You can get away with this for one year no problem, but after that it becomes more difficult.
Volunteer visas are basically a thing of the past because of abuse. But there was a time when this was the go-to for people that wanted to stay here. Basically you paid a charity to again,run cover for you while you stayed in this country long-term.
Then there are the "business ownership" visas that are currently being overhauled by the government. These used to be reliable long-term visas for people that had a bit of money. You would set up a company and then assign 49% ownership of the company to yourself and make yourself the managing director, then 51% of the shares would go to Thai people and in the meantime none of those Thai people actually have anything to do with the company at all. Sometimes the "companies" exist only on paper or they do a trade that was never meant to actually succeed. These are the kinds of visas the government is currently cracking down on.
All of this could be avoided if Thailand had some sort of viable long-term visa that stayed the same and had rules that were clear. I don't really understand why they don't do that. This country constantly whines about how their tourism numbers are dwindling while simultaneously chasing out what seems to be as many people as possible.
It seems like every couple of months the rules change here and perhaps they do around the world. All of us living here have this sense of dread every time it gets close to time to renew your visas and many people really don't know if they are even going to be allowed back in.
As you can tell by the already 800 words this is a very big part of what is so difficult about living somewhere that is not in your passport, especially in Thailand. I end up hearing similar stories about other southeast Asian countries such as Malaysia and definitely Singapore but Spore is one of the most expensive countries in the world so that doesn't really fall into this category. I know a few people that live in Vietnam and just make visa runs all the time and the government doesn't seem to mind.
Cambodia is a bit of a hot spot right now in that people seem to be quite happy with how easy the visas are there but I would be willing to bet that 
Laos isn't interested in long-term people other than highly qualified professionals. I've never met anyone that tried to live there long term. The Philippines seem to be attractive to some people because of visas but for some reason almost everyone that lives there ends up wanting to come back to the mainland. Maybe it it island fever. The same is true of Indonesia. All of these places and other around the world have constant issues for people that are not citizens trying to remain there long term, and at least in Thailand the only way to be secure in your visa seems to be to either do what I am doing and have your visa sponsored by a government entity, or to sign up for their ludicrously priced "Elite visa" which is a blatant "pay to play" situation where the rules no longer apply to you.
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I wonder how many expats there are in these countries? hundreds of thousands no doubt
Even though I am sponsored, I realize that the school has me by the neck if they wanted to be jerks about my employment there. It is always a tricky game with them and everything has to be carefully managed. I don't really have any power and any time there are a lot of new staff members I admit, I kind of worry about them letting me go. They have never broached this subject because they know as well as I do that working there sucks and many, most, or all of the new recruits are not going to last very long once the honeymoon period is over.
This is likely the biggest downside of living in a country that is not your own and it is something that is always on the lips of everyone I know that lives here. If you are willing to deal with it though, and can figure out the right way to make it happen for you, to me at least, it is worth the stress.