I bought my first A500 from a girl who had WALL CABINETS 4 metres by 2.5 metres high with drawers full of pirated software. She threw in a box full of pirated software-mostly games for free. When I saw she had every piece of commercial software ever made for next to nothing I was hooked and ended up buying a 100 or so games from her. But what I found was that games didn't really interest me for long. I think many people pirated games simply beacsue they could, and probably never played most of them much, having it for the sake of having it.
My Amiga habit really kicked in when I got Real 3D version 1.4 off Amiga Format. I then realised that productivity software was what I wanted, and to make the most of it, I needed manuals (and the tutorials in CU Amiga, Amiga Format and ACAR). So I bought legitimate copies of Wordworth (3,5,6 and Office), DPaint 4 and 5, Brilliance 2, Scala 3, Cinema 4D v 4. And HEAPS of software on the magazine covers, some of which I upgraded, for the manuals eg Vista Pro, Image FX.
One app I never purchased was Lightwave, but I did use a pirated copy, but for its plaudits, I preferred Cinema 4D: Workbench look and feel, easier to learn, quality rendering engine, faster interface and faster rendering. So even if I could afford the $1299 asking price, I wouldn't have bought lightwave.