My first Cakewalk version was 3.0 on 3.5" floppy discs. Was running on a 386DX machine with 1 meg ram.
That was pretty much top of the line back then.
The very first sequencer software I ever used was called "The Final Cut" written by a guy up in Canada. It was a blast learning how to program songs. When I first received my copy from "Bananas" out in California, it wouldn't recognize my Music Quest 2Port midi interface. I contacted the guy in Canada and he re-wrote the software and sent me a new version that worked with the Music Quest interface. Finally "upgraded" to Cakewalk 3.0, got a Music Quest 8PortSE rack mount interface.
Those were the days