Micheal: will answer your question asap... I've gotta go to work now
Ok, first of all, teaching in Japan is quite easy (the actual teaching part) especially if you're teaching kids. I think the long-term mental strain of having to be 'genki' (lively, happy) day-in, day-out is more of an issue. Of course, some people excel at being genki, so for them teaching in Japan is a walk in the park. As you'd only be teching part time, you shouldn't hve a problem. Most other teachers like teaching... they say it's easy money, although some can't stand children or repeating themselves endlessly.
About the wine... sorry I don't have any experience importing perishables. Anybody?
As for me, I teach at an English School in Osaka, I also do 'other stuff'... everybody will find out what that is next month.