Docker running on Windows 10 still gives various issues. Although MS does it’s best to integrate docker smoothly on Windows 2010 PC’s, at our company most users that use Docker on Windows experience some issues. Users on Linux Desktops or Mac’s hardly ever experience any issues.
Docker on Windows IMHO is still not mature enough, but once you’ve solved the issues with the Hyper-V configuration, certificates and so on, it runs quite well. I run Docker on linux for over 2 years now and support a Jira, Confluence, buildenvironment and more all running in Docker, and I never experience any issues.
If Docker is a good fit or not depends on your use case and you should (as an architect/developer) investigate the security aspects of Docker. Docker is very useful in a development environment to improve the overall build process, but also in a production environment.
Your issue with the certificates has not much to do with the trusted certificates from your company. Probably you first have to solve the issue with “waiting for ssh to be available” as it seems your network is not configured correctly. This could be caused by an (older) installation of VirtualBox. See also: Docker machine stuck on “Waiting for ssh to be available...”.