If it had that option i would use it for sure,
if that option implies it uses some default settings...
for example, http-server tries to setup in the /public folder if the one you're executing the command from has a public folder. if not it will setup the current folder.
things like that make your tool easier to use, since you don't have to ask for it every time.
such a flag could 'assume' the current folder or the public folder is the one you want to host. if not then people can use the questions to set it up.
sounds feasable yes