First, like I said, most companies in my field (including me) already do a software subscription model. You write "there's no reason I shouldn't keep using it for another 5", but there are reasons to pay for chemfp upgrades even nowadays:
1) I track support for underlying toolkits, where new features are added and APIs change. For example, the most recent release of chemfp added support for Open Babel's 3.0's new circular fingerprints, and for a number of new structure formats in OEChem and RDKit.
2) The commercial version adds Python 3 support - if you stay with Python 2 then you build up technical debt. (#1 and #2 depend on other software advancing enough to need support.)
3) I added improved performance, new APIs, and Zstandard compression support, which resulted in better I/O performance over network file systems than gzip.
So while you could wait 5 years - and it would be cheaper for you to only buy a new copy every 5 years than a support contract - there are advantages to spending the money. And I can still budget for a 5-year update period; while Microsoft has to meet market growth expectations on their revenue streams.
Second, there's plenty of scientific software in my field which started decades ago, and which haven't become "essentially useless" in the meanwhile, making them counter-examples to your broad description.
Third, pharmaceutical companies keep their data close, and prefer to analyze things internally rather than on the clouds. Even the search queries may contain sensitive chemical structure information, which causes some companies to block access to chemical search services unless an NDA is in place with the search provider.