So I connected my Commodore 1541 floppy drive to my PC's LPT1 port using a XM1541 cable and invoked a transfer program called Star Commander, just to find out that Windows 2000's pre-emptive multitasking and asynchronous I/O just won't allow for the kind of synchronous control required to read from and write to the old 1541 drive. Star Commander even ships with an additional I/O driver for this scenario, but still it just didn't work. I had to switch back to DOS (now, this is one thing DOS is definitely doing a better job in), and voila - no timeouts any more.
Besides getting more or less every ancient program floating around on the internet onto my C64, I can as well transfer data from my old C64 disks to my PC, and run it in any C64 emulator, e.g. VICE. Also, most of my friends did not really keep their Commodores for the last 18+ years, so I can provide them with images of their old C64 disks for usage within their favorite emulator.
After Friday's Speedball session, I simply had to try Commodore International Soccer. Have a look, and don't tell me this doesn't beat EA Sports FIFA 2005 by far!