Shareware thrived not in the era of downloads, but in the era of the Floppy Disk.
It wasn't enough to see a game on the net, you played it with a friend, you copied the floppy.
When I was a kid, internet access was still slow and not universal. I had 33.6 dial-up (and so did a few other people I knew) but I was in the minority, and I was connecting the prodigy (and later AOL) so I didn't get The Internet in all it's glory, I basically got web and email.
Shareware games were an artifact of my community (and, let's be real, I was young for that community. Shareware games were an artifact of my Uncle's community.)