I started on Music Creator which came bundled with those midi cab;es via serial port that never worked in Windows. Cakewalk, Sonic Foundry and Magix has boxed software at Best Buy, Staples.
Next was Home Studio and gave a great deal on upgrading to Sonar 2, which is still my favorite because it's not cluttered like most DAWs.
I did skip S6 - they were getting like Finale with paid upgrades every year. That put off some since the new versions didn't fix the problems.
When I bought HS 2002 they actually had demos of other software. I was getting turned off by the cluttered GUIs and tried the lite version of FL Studio that came with HS 2002. I became an FL fanboy.
I don't collect plugins as much as I do DAWs. All I need is a Mac and have Logic, PT, and DP, I think I have them all covered.
BTW Cakewalk was a pioneer in the industry. I do believe it was the 1st 64 bit DAW,