But where's the fun in that?
The biggest challenge with 400K & 800K drives is that first disk. Once the machine is booted up, there's no problem. There exist any number of ways to transfer files, with a properly configured startup disk. Besides, having a Mac with a Superdrive that can run OS 7.5.5 at a minimum makes using a Mac without one moot vis-a-vis your Windows argument.
The most interesting observation here is that Apple came up with a fantastic solution that allowed a 3.5" disk to hold 10% more data, which in those days was a big deal. Yet the PC industry was so confident in their DOS stronghold thanks to the business world's confidence in IBM that instead of adopting the more useful variable speed drives, they stuck with a cheaper fixed-speed model. Clearly they did not see Apple's improvement as any kind of serious competition. Arguably this was not as important with DOS computers at the time since the graphic-less files tended to be much smaller. But, GCR vs. MFM is irrelevant since software exists to write that format on either platform. The compatibility problem between PCs and Macs for half-a-decade was not an encoding problem, but rather the ingenious method Apple employed to cram an extra 10% of data onto the same physical space, resulting in a hardware incompatibility which cannot be overcome on the PC side. For that, I do not fault Apple but the cheap PC industry.
Today I consider the difficulty of getting an original compact up and running a badge of honor for the foresight and level of quality to which Apple chose to hold the computer industry.