Should I install cookbooks from Chef Supermarket to my ChefDK workstation and then upload them to my Chef server or should I just install supermarket cookbooks to my Chef Server? Brand new to chef just playing around with it in my environment.
You cannot "install" cookbooks directly to a Chef Server, they always have to come indirectly from a workstation. The usual flow is that you download them locally from Supermarket and the re-upload to your Chef Server. Tools like Berkshelf and the Chef Policyfile system handle the heavy lifting for you so you don't have to do it one-by-one.