I started a collection of old MP3 players & am hoping to get most models that stored 32 MB & some that started as 64. My main problem is how to get music on & off them from today's 64-bit computers. My latest model I'm wondering about is the Rio 600, which does use USB for the transferring but the player end is proprietary & is not USB Mass Storage. From what I understand the main challenge is finding drivers, if any even exist. The other issue is finding software that can read & transfer contents back & forth.

Besides getting access to a old PC with an old OS provided I have the necessary software for the device, could I use VirtualBox or a similar virtual machine program to interface with the player?

In case you wondered about other players that are even older & used the parallel port for transfers, my current PC still has a parallel port (amazing given the CPU is 64 bit - did anyone even still use parallel or serial ports in 2007?).

Thanks a bunch if you can help. :-)