Given the many different features this is not surprising. My approach was to focus on learning one set of features at a time. I used http://doc.norang.ca/org-mode.html as a guide.
The order I went in was:
Creating / editing / manipulating trees - Being able to easily organize everything in a hierarchy
TODOs - how to customize my own list of TODO states to fit my workflow
Habits - I created a habit for learning more about org-mode each day
Agendas - I found this to be one of the most useful features especially being able to create a custom agenda to see exactly what I wanted - a section of scheduled todos/habits and list of TODO items organized by todo state, sorted by category
Capture Mode - makes adding new todo items easy
I used org-mode to help me learn org-mode, using everything I learned prior to help bootstrap learning the next piece. At the same time I integrated the pomodoro technique into my work flow. So my habit item for learning org-mode was to spend one 25 minute period a day learning. Do this for a couple of weeks, making sure to spend some time customizing everything to suit your process and you should be all set.
I used org-mode to help me learn org-mode, using everything I learned prior to help bootstrap learning the next piece. At the same time I integrated the pomodoro technique into my work flow. So my habit item for learning org-mode was to spend one 25 minute period a day learning. Do this for a couple of weeks, making sure to spend some time customizing everything to suit your process and you should be all set.