Being able to create a new web app as part of an existing plan makes a ton of sense, but I can't help but feel like it would simplify the getting started experience for users if the az appservice web create command would allow you to auto-create the plan for you, instead of needing to explicitly run az appservice plan create before hand. This would mirror the experience in the portal a little more closely, and optimize for single app plans.
I really like how the az acs create command chose to auto-generate a new service principal for you if you don't specify one, and I feel like this is another opportunity to streamline the experience, while still providing sufficient flexibility when/if needed.