May be Coffee House fodder but I had to dig out my Sonar X2 discs to get the Roland R-Mix plug back and thought I'd take a quick pic of my Sonar journey lol - I started with Cakewalk back in the 3.5 floppy days but don't have those any longer (I've seen some of you do!).  X3 Producer is still in the shrink wrapped box.  I didn't order the Studio Instruments but Cake threw that in on one of the orders.  Been a good run.
 
EDIT: just to thank you all for your story and to add that my first encounter was when my wife and I recorded in OKC back in the early '90s when the engineer used Cakewalk for DOS to sequence a few tracks that sounded great!  I was impressed enough to jump on the CW bandwagon.
 

 
 

sonar xl was my first licensed version

fwrend
May be Coffee House fodder but I had to dig out my Sonar X2 discs to get the Roland R-Mix plug back and thought I'd take a quick pic of my Sonar journey lol - I started with Cakewalk back in the 3.5 floppy days but don't have those any longer (I've seen some of you do!).  X3 Producer is still in the shrink wrapped box. 

Sonar 4 was my fav of those early versions

i started back in 2004,using home-studio-2004

Cakewalk Apprentice (1993!) - some Cakewalk Pro version - SONAR 2.0 XL - SONAR X3 Studio - CbB

Cakewalk Pro Audio nostalgia (pre Sonar!)... didn't own any but had the opportunity to lay down my hands on it couple times in late 90'ties and I liked it... multitrack support in PRV was groundbreaking!

Sonar HS 6XL, 7, Sonar 8 Studio, Sonar 8.5 Producer, Sonar X1-X3, Sonar Platinum-CbB.

Sonar 7, where it started for me

Hi. I started on Pro Audio 9 (97 or 98, I believe).. Then i Had SONAR 2 XL and 4 Producer, before jumping up to SONAR X3 which was quite a jump  Went for Platinum when it came out, and now use Cakewalk by Bandlab.
All the best.