My Cakewalk history starts with ProAudio 4 (in 1900 according to my Cakewalk Store account) and is still going strong thru X1 and will continue on into X2.
TBH, I did not really start in earnest until SONAR 6/7 (and for some reason I skipped SONAR 2) as I never had the computing power or interface worthy of replacing my Tascam 80-8 or my ADATS. At SOANR 6 I was ready to go totally ITB.