First Amiga 500

[amiman99]

The price for a working A500 is not bad.

The cheapest way to make floppies is with this method:
http://www.amiga.org/forums/showthread.php?t=62243&highlight=transfer
I personally did not try it (I have A1200 with CF card, it makes things easier), but it should work. You do need a custom cable and a parallel port on the PC.
You also could use slower method using the Amiga Explorer and a serial cable.

You can also get the "Floppy Emulator", more expensive. Just copy ADF files to SD card and select from menu and play.

kipper2k makes 8MB plus IDE upgrade board for A500, this can be useful in the future (or now).

[amiman99]

@Dr.chef
You can not format Amiga disks on WinPC, even under emulation.
You can however transfer ADF file from WinPC directly to the Amiga's floppy drive, using 2 methods: Serial or Parallel.

Or just use the floppy emulator

[amiman99]

As for the price, 100$ is a bit high for stock A500, I believe. Even with a monitor.

In the US they are harder to come by then Europe, the price is based on availability.