Very nice post!
Yeah it was a long time, I don't remember exactly when, it seemed be Cakewalk-Pro Version 2 or 3 for  MS-Windows 3, I think!
 
 

cakewalk 3.0, windows 3.1,  turtle beach multisound& maui, roland D20

1993.  Yep.  And I was old back then when I bought it too...

One of those sound blaster card that came with Cakewalk sequencer in 1998? Then Home studio 2 in 2002? Upgrade to Sonar2 in 2003? No a serious user without a good sound card. Then decided to go serious with 8.5 and follow the grade path till X3 today. Try demo of live and FL but not quite getting the hang of it. I miss PRV view the most. Still a Sonar user. 

bitSync
1993.  Yep.  And I was old back then when I bought it too...

I wasn't old then, but I am now ... I'm a 49 year old Grandpa!  I'll be 50 in December; yikes! 
 
My 10 YO twins are both big into music, so it's been passed on to the next generation. 
 

I've been on board since 6.  I found a class on DAWs at the community college.  I was actually looking to learn about Cubase--it was included with my sound card.  The class was using Sonar 6, so I got 6XL.  They were using 6PE.  I could do some of the basics, but I didn't have all the plug-ins to finish the assignments at home.  About half-way through semester, Brandon did a presentation on 7 and made an offer I couldn't refuse on 7PE. 
 
I probably wouldn't upgraded to X-3, but I'm a little short on cash right now, I have to upgrade my hardware to take advantage of all the features.  Hopefully, I may do it in January if they still have any good deals going. 

I got a lite version of pro audio 8 with my sound blaster card years ago. I think it was called Cakewalk Express Gold. Up until that time I was just recording analog. 4 track porta-studios (tascam) and reel to reel machines. I messed around with the software but at the time I was also beginning to get a handle on basic computer skills too.
 
From there I went to guitar tracks pro which was a lite version of pro audio 9. After a brief time of using it I jumped to Pro audio 9. From there I went to Sonar 2 SE. Then I upgraded to Sonar 3 SE, and finally I made the jump to the producer edition of Sonar 3. I then went over to cubase and then pro tools for a while.
 
Then I came back to Sonar 5 PE. This edition was the best by far. I don't remember the version of Pro-Tools or cubase that I used back then but I liked Sonar 5 better. As I look back I remember that particular upgrade being the game changer for me. Cakewalk had just come out with 64 bit recording at the time. My mixes were sounding much better on that version of Sonar. Older recordings were remixed with better results. I did a lot of recording with that version.
 
The next upgrade for me was Sonar 7. I had some issues with Sonar 7 and went back to using 5. Then the bakers released some updates and that seemed to fix the problems I was having with 7.
 
When Sonar 8 came out I just had to have it so I upgraded again. I really liked Sonar 5, but I thought Sonar 8 was awesome for its time. I have been updating on a regular bases ever since that version and I will probably continue to do so.
 
I have used other DAWS but for me personally Sonar seems to be a better fit for what I do with music. I now look at Sonar X3 and I am amazed at how far things have come even from when I was using Sonar 2 years ago. It just keeps getting better and better. As long as that continues I will be a loyal customer.
 
I don't have any issues with X3, but I must admit I don't take full advantage of everything this program can do. I don't use all the features, but for what I do X3 is my choice. Awesome software indeed!
 
 

eric_peterson
I wasn't old then, but I am now ... I'm a 49 year old Grandpa!  I'll be 50 in December; yikes! 

50? Pshaw. You're a spring chicken, sir. Revel in your youth!

 49 here too, by revel, I hope you mean I can take a nap now...
 
 Cakewalk user since Guitar tracks 2.0 and win 98 days. First MIDI capable DAW was MC4 then went to Sonar 7 studio, 8.5 Pro, X1,2,3  I don't know if loyalty is a good word for it though, CW is the DAW I am most familiar with and guess I'm just too damn lazy to learn another