When you move to a new application platform, you have to work with a new set of artifacts and new operational processes. If you currently use the Windows installer for deployment, your artifacts are Wix files and MSIs. Your deployment process is to copy the MSI to the target server, log on, and run the installer.
After the move to Docker, you will have Dockerfiles and images as the deployment artifacts. You push the image to a registry and run a container or update a service to deploy the app. The resources and activities are simpler in Docker, and they'll be consistent between projects, but there's still a learning curve when you start.
Containerizing an app that you know well is a great way to provide a solid basis to that learning experience. When you first run your app in a container, you may see errors or incorrect behavior but that will be in the domain of your own application. When you're tracking down the issue, you'll be dealing with an area you understand...