I have been using Twelvetone systems since the Korg M1. My first major 'personal' daw purchase was HS8 and then the late great Pro Audio 9. I have maintained and upgraded Windows and Cakewalk at the 'producer' level, as well as hardware (which unfortunately is inescapable) from Sonar 1 and on, and I feel comfortable with Cakewalk's understanding of Windows.
Granted, I'm not sure even Microsoft understands Windows....
Almost each and every year, I would drop about a buck fifty to upgrade to the latest and greatest, mostly because it behaves with whatever current Windows OS was on the grid.
This hasn't changed for me. I own Sonar Platinum. It performs (for me) better than it's predecessor, and that's why I upgrade.
Payment/subscription/membership.....moot
Freebies/3rd party/limited time offers...moot
just my two cents....
AF