My first PC, which had an i486 DX4, a Soundblaster AWE32 and ran Windows 3.11 for Workgroups, (we're talking a very long time before my hair went grey!) came with a version of a Cakewalk / Twelve Tone Systems MIDI sequencer on floppy disk. I don't recall what it was called exactly. So that was my first experience with anything Cakewalk. However I first bought Sonar 3 and then every version since.

I started out as mainly a session guitarist and keyboard player. Out of curiosity, I started learning on analog tape. I made the transition to Adat and Tascam digitals. The studios I worked at started making the jump to Pro Tools, Saw, Samplitude, Logic, Cubase, and Cake. My first experiences with Cake came about 1997-98. I was hooked. I always had access to the studio computers so I learned as much as possible at work. The studio I worked for continued to do upgrades so I had access to all the upgrades up to Sonar 6. When Sonar 8 came out, I knew it was time to set up my own project studio at home. When I bought Sonar 8, I got the free upgrade to X1 and I will continue to use Cake until they pry my dead, cold fingers from the computer keyboard.
I hate sounding like a fanboy but I have been totally sold on Cake products for many years. Pro Tools may still have the standard but Cake has been slowly closing that gap. I am anxiously waiting until I finish a project this month in order to get X3. 
Don't get me wrong! Cake is not perfect but from my experiences, neither are the other softwares. I will stick with the devil I know for a long time.

Cakewalk v1.0 on a 5.25" floppy disk's

I started around 1991 with DOS 3.5" disks from Twelve Tone Systems. I had a basic MIDI interface and routed audio out from my Roland JV-80 to a boombox. That setup worked great.
 
Every new version announcement has had something that really appealed to me, so I've always upgraded. It's a combination of loyalty, good vibes about the company, and the fact that the product works for me.
 
Mitch I.

Must be around 1991 - Cakewalk 3.4 on a stiffy, running on a 386 machine with a 40 MB HDD if I recall correctly. I still have the disk somewhere! I think I still have the manual too... Any antique collectors, now's your chance to get a killer deal! :O)

I paid $400 for Cakewalk Pro 3.0 in 1992, along with $2000 for my 486SX! My friends were in envy over the 2MB (yes, megabytes) RAM and the mammoth 120MB hard drive!! My controller was an Ensoniq ASR 16 sampler...still have it but the disc drive is toast.

Geez, you guys sure are some 'old' DAWgs....

CWPA 4.5, I had 16mb RAM.

Loyalty eh?



 
 
I used for about a year Cakewalk in 1995, I can't remember what version but it on one or two floppies, and no (sorry) I didn't pay for it! I hope I'm forgiven but it was an excellent marketing ploy as I ended up paying for it.


I used Sonar 2 but didn't really get to grips with it.
Then came back to X1.

Otherwise it was tape and desks.

I have been here ever since cakewalk 3.0 on floppy disk.
WSS