I ellipsed all the SD card mention, but I find this summary of the situation fascinating, as this is pretty close the world we have today for a lot of people. Mobile phone is the dominant form of internet connectivity for a significant portion of the population.
An insight from that could be that Japan didn't create the iPod because that global need didn't make as much sense in the context.
I personally think it is really Sony being way too confident and stubborn, preventing the digital walkman from being the universal player it could have been. What they had was somewhat good enough for a big span of the Japanese market, but way too clunky and outdated for the rest of the world; and their position as an incumbent made it harder for smaller company.