I was in Hokkaido many years ago for work and loved it. Compared to the rest of Japan, indoor/outdoor spaces are wider, food is better, and people are friendlier. I never could swing another work visit, so I dream about spending time there in retirement.

I could imagine, though, that companies might have trouble attracting quality talent to Hokkaido, because people see more opportunities in the big cities down south. I suppose it's like if you were trying to build a tech hub in Montana.

It's not landlocked and less isolated than Montana. Montana is beautiful in select parts but it's also a little bleak. Hokkaido is still a lush island and Sapporo is a proper city. I'd say it's more like getting companies to move from SF or LA to Seattle.

The same could probably be said of many areas of the US (or other countries). Good outdoor recreation opportunities, some good local food options, but not a huge number of (local) employment opportunities or the nearby options that density brings.

As you say, if you can work remotely, it may be fine but it's a different situation from working in a hub of whatever your specialty is.