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They already put the fine print saying Stadium won't have transfer, so I wouldn't count on that, even if it is feasible.
Yes, but that was likely put in place at the time because there was no GameBoy app for the Switch so the Pokemon games couldn't be on the Switch to begin with. Now that we have the app, it could be a different story.
Now, we may end up in a situation where it doesn't matter anyway, but I'm not 100% ruling it out.