Have you made any progress on item 1 here? I’ve run fastai1 models on windows before so I think the answer is ‘yes’, but with version 2 I’m running into the same problem you describe. It seems similar to this v1 issue: https://github.com/fastai/fastai/issues/1482
If I understand correctly, the workaround is to use learn.save instead of learn.export. However, when loading the saved model with learn.load, you need to separately define the databunch (which translates into version 2 dls?). In version 1, there’s the ImageDataBunch.single_from_classes method to make a learner that’s ready to load a previously saved model. Anyone know whether there’s an analogous strategy available in version 2?