Using a crack has both legal and security implications for the company and therefore at least in my place of work can result in serious consequences for the employee including termination of employment.
Most of nag screens implying that you should buy or uninstall software in 30 days or something like that. It's written in license. They just don't enforce it. So violating license is acceptable while cracking is not?
Sure, but you have to multiply that with the (perceived) probability of it being an issue with the expected benefit. That is probably a calculation that often comes out as "get it, dammit".