Another thought, especially if you're primarily moving files from the PC to the Amiga. Write the files to a CD. Get a CDrom drive (like A570) for the A500 to read them. You could put the OS and apps and games on one CD.
I think you can make a bootable Amiga CD on a PC but, if not, you can boot with a floppy and then transfer the system to the CD.
Having a CD on a 500 makes a lot of sense.
Money + availablility will be the main factors. A good SCSI interface for the 500 would be ideal, you could add a Zip, CD drive, etc. As for Zip drives... also ask any computer-owning friends... I was at a buddy's house recently, he replaced his old PowerMac a long time ago... still had a SCSI Zip drive, CIB.... He gave it to me for free.... (It's on my WarpEngine 4000D)
