I bought CAKEWALK 1.0 in Dec 1986 and used up until 1992. It never occurred to me to upgrade. The manual was a small pamphlet. My computer was an Amstrad PC with 256 KB of RAM and a 20 mega byte hard drive!
 
Here's a surviving project: http://www.soundclick.com/player/single_player.cfm?songid=5265795&q=hi&newref=1
 
All instrumentation was sequenced on CAKEWALK, which was played (through a rack of outboard gear) & recorded in stereo on tracks 1&2 of my TASCAM Portastudio, where I recorded the vocals (analogue of course) on tracks 3&4.
 
Cheers,
 
Bert