I don't have any international music performance experience, but I do know that getting gigs is all about connections. It seems to me that making those kinds of connections, hard enough for an American in America in the place where he's lived for 20 years, will have an added layer of challenge with a language barrier and culture barriers ranging from the relatively modest (American in England) to the large (American in Japan). Are you a social? Super extroverted, yet able to read the room and tone your approach to local norms?
I have also read - and another poster alluded to this with reference to the fact that governments reallly do check visa status and it's much harder to fly under the radar - that at least in Japan, "English Teacher" is/was mostly under-table work, likely to involve all kinds of scut work, and without legal status. So immediate deportation was always hanging over a large number of those "English teachers". OK for a 20-something that just wants to live in a foreign country for awhile, live on ramen noodles and weak green tea, no assets, no plans, just hangin'. Not so OK if you have assets and career plans.
I have also read - and another poster alluded to this with reference to the fact that governments reallly do check visa status and it's much harder to fly under the radar - that at least in Japan, "English Teacher" is/was mostly under-table work, likely to involve all kinds of scut work, and without legal status. So immediate deportation was always hanging over a large number of those "English teachers". OK for a 20-something that just wants to live in a foreign country for awhile, live on ramen noodles and weak green tea, no assets, no plans, just hangin'. Not so OK if you have assets and career plans.