It should be illegal to sell someone something they do not own. In your windows/office example, I’d say it should be illegal to crack/copy the software, but it should also be illegal to sell the software without an offline method of permanent and irrevocable activation (think offline cd keys), and it should be illegal for a company to put any barriers in front of use (vm, laptop, server, cpu cores, memory limits, etc) and illegal to put any barriers in front of resale. Selling a windows update, or a subscription model to updates seems completely reasonable (and probably should do online blacklists for shared keys) but the fundamentals of ownership shouldn’t be eroded in law.
In the tesla example, your car should be your car. If you can modify the software to give you more features that’s your car. If tesla wants to sell a subscription to incremental upgrades on their self-driving algorithms that’s fine, but they should be liable for any faults in older revisions if they paywall updates. That incentivizes them to do the software equivalent of a recall when something is egregiously or dangerously broken, and also incentivizes innovation because they can’t sell you an update if it doesn’t contain anything valuable.