There are thousands of people using Xibo that don’t find it so - however there is always room for improvement 
We have a feature improvement to add something called Playlists - see Playlists Blueprint, there are many extensions and associated ideas that I believe solve some of your concerns.
Also another for showing some more information on the schedule page: Calendar Overview should indicate the start date/time of each event
You can upload directly to a Layout, which removes one of your steps. There is also an extension to the playlist feature above that will allow a start/end date to be specified there and then… however the overriding principles of Xibo are that it is a structured system which helps you to make sure the right things appear in the right places - we aren’t ever likely to support an “upload and show” mentality.
If that is something you want you can leverage the API to code a simple interface which does all the “steps” for you in one go.