It is sort of funny that the one type of software that manages to get any momentum behind it for this sort of thing—games—is really pointless (I enjoy games too, I just don’t think preserving most of them is a big deal).
For work software, it definitely should be able to run locally and without any license server or whatever. I’m baffled by people who don’t feel the need to own their tools. Open Source software mostly seems to fill this gap for me, but like most of the folks here, I only really need programming tools, which are over-represented in the open source ecosystem for obvious reasons.
Proprietary “freehold” software, I dunno. It could be interesting. I guess I kinda feel like: if your software isn’t going to do DRM, talk to license servers, or whatever, I guess your business model must include the fact that people will probably make unauthorized copies of your software. So, maybe just open source it? Then you have the classic “building a business on my open source library” problem, which is very hard, but at least you have lots of company.