Paul P
Cakewalk's openness is always welcome and makes it easy to figure out how our needs and desires interact with yours. However, there seems to be one aspect of all this that isn't getting much consideration, and that is the buy once and live with it for a long time scenario.
If Cakewalk disappeared and nothing more happened with X3e, I would continue to make music with it. I don't encounter show-stopper bugs in what I do, just occasional annoyances...but I encounter that in all software, so that sets my expectations.
If what you have works, you can keep using it. If you want to buy a new version, I would
assume Cakewalk is realistic about recognizing bugs will surface after a product release, and provide some way to offer users fixes for "show-stopper" bugs. There's no question X3 had some issues, but by the time X3e rolled around, there was justification to SONAR veterans saying they felt it was the most stable release yet.
What's more likely is that you won't encounter problems going forward with Sonar, but from plug-ins that are yet to be developed and operating systems that don't exist yet. Dealing with those scenarios requires development work, which doesn't come free. I can't imagine a scenario where a company making software today will be issuing free fixes for products that were released in, say, 2013 in order to retain Windows 12 compatibility.
Just FYI - one of the reasons why you're seeing less development of "pro" iOS apps is because companies I've talked to (not including CW FWIW) are tired of having to update the program every time Apple makes some slight change to iOS, yet customers expect the update to be free. They simply can't afford to operate that way.