My first Cakewalk purchase was v. 1.0 for DOS, on a single 4.25" floppy. I used it with my brand new Ensoniq VFX.
The next big change was Cakewalk for Windows (Win 3.11 at the time). I got that and upgraded through several subsequent versions. I remember getting on the Cakewalk Compuserve forum, where Greg Hendershott would show up from time to time.
Years later I became aware of Cakewalk Pro Audio (digital audio recording!) and picked it up. It was version 4, I think. I tried it out with the SoundBlaster that I had installed, and that was the beginning of a series of purchases that has never ended - audio interfaces, microphones, preamps, mixers, monitors, plug-ins. I have bought every single release of Cakewalk Pro Audio and SONAR since then.
My home recording adventures go back to two channel sound with sound machines and (the big leap forward) a Dokorder four channel tape recorder. I learned all kinds of strategies for getting along with four channels, explored the limits of bouncing tracks, etc. etc. I never dreamed of being able to do wihat can be easily done now with SONAR.
I imagine that it can all be done with other DAWs as well. But Cakewalk/SONAR is what I've learned on. And the learning curve has been especially steep with the X versions, because of their increased power. Collaborating with people using Protools is no problem, as I can export OMF files or just wav files. So although I am mildly interested in the competition, they would have to offer something very interesting indeed to get me to switch at this point.