I know using a real disk on a real AMiga has some sort of joy in it, but why not just stick to a later version of WinUAE since you have a PC? Its got to the point that it runs games better then many real high powered Amiga systemm do. I used it a lot for games since many didnt like my A3000.
If you plan to move a lot of files over from ADF why not get a catweasel MK III flipper? You can use it in WinUAE to write the ADF from emulation to a floppy as if it was an Amiga then pop it in your A500. They are less then $100 now.