I’d think you would be able to see it easily from space. The ISS is only ~220 miles off the ground. It would be about equivalent to writing it an inch across and looking at it from 7-8 feet away.
The distant pics are from satellites, the close-up ones are from aircraft. You can usually see the “jump” in quality as you zoom in. Some areas only have satellite imagery, and you can’t go “high-res”.
E.g. see here. This spot has (not great quality, admittedly) aerial imagery. Scroll a little way to the north and you’ll see that runs out and there is only blurry satellite imagery, which looks OK when you zoom out.
As for the map detail, I believe Google users can add their own detail for roads etc, as a kind of open-source project. I know they do that a lot in third-world countries where there is not very good “official” mapping available.