Something I would note to maybe add a bit of perspective is that Cakewalk's method of "fixing bugs and adding features" is pretty common in professional software, as is maintaining only the latest version. At work the researchers make a lot of use of Matlab, HFSS, and Cadence and if you think you've seen expensive software, you ain't seen nothin' until you've seen the price tag on those. They are subscription models, you have to pay yearly and if you don't, your license expires and you lose all access to the software. New versions come out at varying rates. Matlab likes to do one twice a year. No fixes in-between, twice a year only. HFSS is more traditional, you get a new major release once a year or so, and then maybe a couple fix releases for that (two is the most I've seen).
What is common is as soon as a new version comes out, development of the old one stops cold. Ansoft doesn't release any point release fixes for old HFSS versions, only the latest. Matlab is more or less a continuous development model where a version gets released and then they just start work on the next one. They allow you to download their older software, usually quite far back (Mathworks will let me go back to Matlab R11 which is from 1999) but there's no support in terms of patches or the like. You can use the old version if you've code/models that need it, but it is what it is and is never getting changed, only the new version is under development.
It's just how it goes with what companies choose to spend resources on. They spend development time on the current version, not on old ones. Really the only major exception is the big OS vendors, and they have rather a lot of resources to do so. Even then only MS really does what many people seem to think should be "standard" which is support all their old code bases for a long time (10 years in MS's case) for a single payment. Apple only supports two versions old, or about 3 years, RedHat supports RHEL for 10-12 years but at a cost of $350+ per year per server to maintain support.