I know you were not comparing Cakewalk with IBM, but rather just trying to relate to your own life experiences, but we must acknowledge that the two have very different business models.
When you buy a large system from IBM to run your business, you also purchase an annual maintenance contract that may cover anything from telephone support to onsite software installation to free software upgrades. When I worked for a mainframe manufacturer, it could cost as much as $30,000 per
month for support, and for that you got 24x7 coverage, including a technician onsite at 3:00AM - I know 'cause I was that guy who'd show up at 3:00AM - plus spare parts stocked locally if not onsite. We officially supported three major revs back on the O/S, and upgrades were "free" with the maintenance contract, so everybody got upgraded every 18 months.
Cakewalk, OTOH, gets 500 bucks up front and that's it. If they want any more $$$ from you they can only encourage you to upgrade or buy add-on products. Unless they decide to adopt a subscription model, it'll always be that way.
CW
support is actually pretty good for this type of low-cost consumer product. But that's a separate issue from having Engineering provide bug fixes for old revisions. I completely understand how they wouldn't want to throw money and resources at a product that will never generate another dime for them.