The problem of file version dependencies has been around for as long as late-linking has, going back at least to Windows 3.1. There's even a long-established name for the phenomenon: DLL Hell. I remember dealing with similar issues even before Windows existed, when I was doing O/S support for a mainframe manufacturer.
When I first starting distributing my own application back around 1996, my business partner did most of the installs. We pulled more than a few all-nighters back then troubleshooting DLL conflicts, he in some remote city, me back here on the phone.
I finally wrote a diagnostic program that finds all of our program's dependencies and their dependencies, compares versions to what we expect, verifies that registered libraries have been registered, and enumerates duplicates. This diagnostic was then incorporated into our standard install so that every workstation has a copy. DLL conflicts still occur, but now we can quickly identify and fix them.
Over the subsequent years I've extended that approach to make my application largely self-diagnosing, self-documenting, and in some cases self-correcting. I don't have as big an installed base as Cakewalk, but I couldn't possibly support as many remote users as I do without some software assistance. If I had as many seats as CW has to support, I'd definitely make my product self-diagnosing.
Adding minidumps at SONAR 8 was a big step in that direction for CW. Prior to that, figuring out which plugin had crashed the DAW was a guessing game. If I were in Noel's shoes I'd be looking at automated diagnostics such as a version checker, a debug logger and perhaps a basic minidump analyzer, and bundling them with SONAR. Their support staff should be lobbying for this, too.