I used to be an amiga cracker ran a fairly successful bbs for about 3 years, and I've also worked in the games industry (but not any longer).
I dont regret doing the cracking, I always did it for the challenge and it was fun.
I did however start off supporting my modem trading habbit by selling the stuff I downloaded to the local market trader.
Thats the only thing I regret. I stopped doing that as soon as I was about to afford to support my phone bill by myself.
I still dont buy any software but i'm not involved in any cracking these days (apart from maybe the odd bit for my own personal use).