The problem is diskettes are crap and phasing out and WHDLoad on 2MB certainly is quite annoying, I usually find no game that I can run without annoying OS flashes. Particularly annoying in my CD32 (here's hoping that CD32 expansion gets finished).
I think the best option for newcomers to the Amiga who want to use the machine they found in the attic or stuff like that, is to get the HxC floppy emulator. It's the best of both worlds: you don't have to deal with floppy disks and you don't need extra RAM to play stuff on an A500. Yeah, loading times, but we used to endure them, didn't we?
I don't really see the point of kickstart switching in the A500 though, specially if you have no accelerator.