I will take a slower approach by training in Japan, learning the language, and forging industry connections over a couple of years before purchasing a machine.
That is a very sensible approach to the problem.
One more thing. Don't think that there are many fresh opportunities in the helicopter world. Every niche has been exploited or somebody is waiting that another operator is going out of business and taking its place. You can be absolutely sure, that the company already operating in Hokkaido, has tried everything to get every possible permission. As far as I know, they have very few landing spots, some say just one. That is all they got after many years of operating there.
The times where helicopters were new and everybody tried to find new business opportunities are over. We now know, what works and what not. The regulations are tight and that is because they have been written after we found out the hard way, what does not work. If you have your sight set on heliskiing, stay in Canada. If you go to Japan, because you want to have a life there, open your mind to other possibilities, than heliskiing, which for a pilot is rather boring and for many companies just the job for the winter. The opportunity you believe to see, to fulfil your dream, has probably already been recognised by somebody from the industry and they found out it isn't worth the hassle.