When I switched from the C64 to my first Amiga I made the choice to only go for purchased software. It meant I didn't have all the latest games, but it did mean that I really had time to play the ones I had. Back on the C64 when I had loads and loads of tapes with pirated games I really only loaded them up, played for a minute and said "Next!".
For productivity software I mostly relied on Amiga Format and CU Amiga cover disks. 
I only snagged one or two copies on the Amiga after making a similar decision. I purchased PageStream after having used it a while and my little sisters didn't get much enjoyment out of Mixed-Up Mother Goose anyway.
In those days I lived off of what was uploaded to the Aminet and played unregistered shareware quite a bit. I didn't miss the Warez as much as I missed watching the cracktros at the beginning of the C64 pirate software I used to use. My internet provider limited my access to a half-hour a day on the freebie rate so time-outs on the Voyager web browser and Miami didn't bother me much even after my hard drive crashed with the AmiTCP shareware version that took so long to set up went with it.
Eventually all of the software I had wanted to register went freeware anyway: Deluxe Galaga AGA was briefly before the author reinstated a nominal fee due to the emulator users' freeloading. AmosPro is still freeware.
The only software that I didn't get because I couldn't afford it was the GameSmith developer system that came bundled with special versions of the DevPak assembler and the DICE C compiler. It took me a while to learn C and Assembly so I'm not sure if it would have helped me anyway. I am not much of a pixel-artist either.
