When I first got my Amiga 500 there was very little on the shelves anyway and I certainly had no access to pirate games. Over the next couple of years I spent an absolute fortune on games and software, and I've always liked to own the software I use.
One of the turning points for me though was when the shops started to refuse to allow you to return games just because you thought they were crap. Upto that point (probably 88/89) you could return a game with the reason that you didn't like it. Anyone else remember that ?
By the time I had an A4000, I had some mates that could get cracked copies of virtually anything and one of them got sent parcels of cracked software to distribute every week. I pretty much stopped buying software for the Amiga.