Not to mention that he seems to be trying to move there without being hired by the JET program, which makes it so much easier for foreigners to get set up. They and the Korean program (which, amusingly,
does market itself on the whole 'Come and teach in K-pop/K-drama land!') are probably some of the most reputed EFL teaching gigs for this reason, they hold your hand a lot and have so much trust built up there's very little risk of a rug pull, misleading job description/accommodations, and in some countries, indentured servitude. It's also not meant to be a long-term job.
Aside from the people, who are often willing to talk to you if you can speak the language competently, and aren't a weaboo cretin but can also equally be unwilling, and you always will be an outsider, the biggest hurdle is just how unaccommodating they are to foreigners outside the usual places, and this is usually not from a place of xenophobia but just a complete lack of thought for the presence of foreigners. Filling out bank forms and come across difficult kanji? Hope you have your phone, pal. Many such cases. For how long Cheebs has been studying Japanese, with professional help, he speaks too slow imo and is either getting scammed or not putting in enough effort, so doing a lot of the things the JET program takes care of will be very difficult for him. He will likely have a very hard time getting housing and residency, not to mention that he's almost a stereotype to them and the places you can make friends (i.e, your neighborhood's bar, very normalfag places) he has no interest in. Although for him with the way he describes mundane social events that he doesn't expose himself to unwilling people as idyllic core memories from movies this may not be much of a change for him.
If he's dead set on this another option for him would be joining Zen Buddhism in some capacity, as Zen is popular in the USA, and they make it rather easy to do retreats/be a monk (temporarily, even) for gaijin, but I doubt he would do this because he can't exactly meditate and then hit Aki. I have a feeling nothing will come of this, much like the Florida move which I suspect he maladaptive daydreamed into reality based on throwaway comments his friends made about sharing a mortgage, it will probably fall apart if he makes a serious effort at all. However, knowing Cheebs, he has an uncanny ability to produce milk when you least expect it, so something may come of this.
Still, with his infamous online presence, I suspect he will get caught by the
Kanadajin filter when trying to get some sort of long-term residency.