I know you asked for (at least implied) the _one_ most significant gadget/event/feature, but I only have the energy/initiative to narrow down to four.
1) The release of Cakewalk Pro Audio, meaning that I (and countless others) could go non-linear & non-analog, ditching the tape recorder and the smtpe striping and the splicing block. For better or worse? You decide!
2) The "Project 5" era, when Cakewalk tried to expand outside its box (and its comfort zone) into new audio technology areas. With the actual P5 program, I include all the RGC audio stuff that came with it, including those trusty synths that became, and are still, a mainstay of creativity for me .
3) The regular inclusion of different third-party plugins, even (maybe especially) the "demo" versions. CW introduced me to PSP Audio, for example, and Melodyne, and others, which are now part of my, er, "signature sound".
4) The people I've encountered in these CW forums and their advice, tips, insights, philosophizing and dust-ups. Goodness golly, what a treasure these posts are (Um, I don't have to include the Coffeehouse in this, do I?), what an influence on my mixing (and a lot of other more-or-less audio/music related topics)! [Swell the Max Steiner score.]