End of support for Windows 10 is Oct 2025. In terms of Windows 11, I am trying to look ahead where I can. Make no mistake, a subscription plan is renting. In all seriousness, I would rather buy something than rent it - even if it means using old software.
On the other hand, if I am doing a series of small standalone drafting jobs - and the client does not care what version of CAD I am using - then I would use just use Acad 2016. If I decided to start my own company doing contract drafting work, then yes I would sign up for a subscription. The Autocad 2016 is my personal copy and is not needed for business so I don't need to keep up with the latest and greatest.