All my Amiga OS's are legal: OS 3.1, 3.5,3.9; Amiga productivity software I use frequently is legal: Cinema 4D, MakeCD, Wordworth 7 Office, Scala DPaint Brilliance PPaint, Ibrowse 2.4, Clarissa
I still have a tonne of other pirated amiga stuff but I hardly use it: Photogenics, ImageFx, MiamiDX
I have NO legal amiga games, but TBH I hardly play them, except for Deluxe Pacman and Deluxe Galaga.
Win XP, Win 7, Office 2003 all legal, but a MS employee gave them to me with licence keys for free.
A copy of Cinema 4d 5 for PC i got off a magazine and I use it a lot more than a pirated copy of C4D v 10. Tons of emulators with pirated roms, but I have the originals (SNES, N64, PSone) as well which I prefer, mostly.
My net and email stuff is on Ubuntu exclusively, and thats all free.
My rule is if i use it regularly I'll buy it.