"Regimented"? I comment that you're posting in the wrong section for a reason: if some people look in the correct section, they will not find your questions and not be able to give you the answers you seek.
I asked about a silly diversion just to know if you are serious about keeping your own thread on track. I could have joined in and shown you even more humor than you could imagine, but I chose to respect your initial query, especially since darned few have chimed in to help you out. I didn't want to contribute to taking the thread off-topic. Is that all that bad?
Forgive me, but I don't know what "I'll take the p\&s" means.
I'm a little older than Mike, married with a kid younger than his, and I have little exposure to fellow foreigners, too, but that's mostly not choice. I live in the boonies. As for having anything/nothing in common with the 22-year-olds, about all I have in common is the profession (teaching English), and it isn't that strong a connection because I haven't done eikaiwa in over a decade, and I was actually serious about the teaching, unlike most eikaiwa instructors I've known. Regardless, I can't imagine having all that much in common with anyone that much younger than me anyway. Huge generation gap.
(F.O.B.???)
There are probably quite a few success stories of foreigners here. Mike is one of them, obviously, and a very good one. I've been here 14 years and am quite happy and secure, so I suppose I'm another, although I don't own my own business. I know some people who have pottery shops or river rafting ventures here in Hokkaido. One guy also has a service to make announcements about job openings and personal ads. Some people do part-time wedding officiating. Some own their own schools to teach English (usually to kiddies). One guy I know sells used cars. The stories are out there. Without looking back on your OP, could I ask you to take a moment to post here (in this fragmented, somewhat tangented thread) just what it is you are seeking from foreigners here?