I had gotten a RealAudio (remember that?) file of Orange Romeda and was hooked, and longtime forum member SPD sent me his Matador Records copy of MHTRTC - this must have been around late 1999/2000ish. Hooked ever since.
Fairly certain my first portable 'digital media player' only took .ra files. Very specific memory of trying to fit just one album (Luke Vibert & BJ Cole's 'Stop The Panic') on the damn thing, using a honkingly low bitrate from the CD rip, and failing miserably due to the tiny capacity.
I got a taste of it when I dove into p2p network sharing back in college - shitty encoded mp3s, 64 kps rips, .wma to some degree. There was time everyone was watching movies that could fit on a CD - < 700 mb .avi files. Saw Akira and Requiem for Dream that way in college, downloaded them from DC++ via a super fast intranet server. (It was shut down a couple years later)
But otherwise it's an era I missed out on. I love reading about the various formats people came across in the nascent days of file sharing. Digital lo-fi music as a format is talked about very little among people, perhaps it will crop up in the future.