Longtime lurker, first time poster
I switched to Cakewalk sometime in 1991, I think, maybe a little earlier. I am not really sure of the exact date. Anyway, I have a copy of Electronic Musician from August 1991 that I seem to remember using to make my product choice (the article also had a selection of sequencers for the Macintosh, Amiga, and Atari platforms). Or maybe I was using the article to check the features of my sequencer against the competitors. I recently found some copies of .wrk files that indicate the were last modified in January 1992, but I am not not sure how accurate that is. Those files have been dragged around from computer to computer and saved and resaved. Maybe there was an earlier .ext that I don't remember. I remember that my first Cakewalk had 120 ppqn and ran just fine on my 486 50 machine.
I wasn't really on any sequencer software when I switched. I had been out travelling in bands playing bass during the late seventies and early eighties (the "disco wars" period, when men fought againt the tyranny of the steady thump thump thump thump of the Altec A7 sound machines and their evil minions, the DJs), and I finally gave in and left the road to return to college. My father was a community college computer teacher and he had Orch 90 on his TRS-80, but that had to have been in the mid-to-later eighties (he died in November 1987) and I just messed around with that when I was at my parent's home. I do still have one file that I painstakingly transferred over to Cakewalk that was originally on the Orch-90. The "solo" on that piece is an interesting construct, very angular and disjointed; I think the input method probably influenced the outcome on that solo.
Anyway, in the period just before I purchased my first Cakewalk I was just using Cool Shoes Drummer to jam with. It was great to have a reliable, albeit if a bit stiff, rhythm partner. Getting Cakewalk really allowed me to add chords and lead lines. I just used it as a "jam machine" for a while then started writing midi pieces.
From there, my story goes like this: played in various bands, 1993 got married (me age 37 wife age 22-she asked me to marry her), 1994 stopped playing b/c wife wanted me at home (swore this would never happen), 1995 still jamming and writing midi pieces, 1997 less jamming, still writing midi, 1998 got Pro Audio, not really able to use the audio b/c my computer was not up to date, got a better computer in 1999 but my wife and I started playing online RPGs, still writing midi, but more into gaming, wife became one of the top players on her server (in DAOC),
10/16/05 wife told me she was leaving me for another "l33t" gamer, and on 10/30/05 I upgraded to Sonar 5 Producer and decided to learn to play guitar and devote the rest of my days to writing and creating music. 06/01/06 wife moved out (she was nice enough to take the SUV and leave me the house) and I started playing music as a 'fulltime" avocation. I work my 9 to 5 and then come home to play. I am back playing in a band also, but have been converting all of my old midi files to Cakewalk projects and switching the sounds to use Dim Pro, Rapture, et. al. and MiroSlav Philharmonik. I started the conversion process in late 2007; the files are arranged in alphabetic folders: last night I finished the T song folder. I tend to get involved with writing new sections and expanding the pieces so it is slow work. And the there is always the temptation to jam.
The last time I counted there were over 800 files. These range from 8 bar drum patterns (not many of those) to eight minute pieces. I try to average writing or significantly rearranging one (song, work, piece, jam) per day. 99% of these things have only been heard by me, God, and the cat (who was part of the reason I got to keep the house).
I am seeing the light at the end of the rearranging tunnel and hope to someday post some songs somewhere on the internet. I have blues, funk, rock, latin, etc. pieces and a lot of attenpts at writing orchestral pieces. Most of it is still just midi, but I have been learning to record audio. As I indicated above, I have been lurking on these boards for a long time, and I have learned a tremendous amount from so many of you. This to me is a very special community.