The "Simplified Workflow" is a workflow like any other i.e. you can edit it as you like, add validators, post functions etc. exactly as for any other workflow.
The "Simplified" part as I understand and use it is more to give users a way to edit a workflow to their liking first, then contact an expert to get any other bindings done right.
For example the simplified workflow resolve status field is (or was at least in earlier Agile versions) not updated when closing an issue. There you had to edit the workflow to add a post function to set the resolve status to e.g. "Fixed".
If adding transitions would make the plugin think it is no longer "Simplified" I have not tested but then again I see the options as a way to let teams experiment and lock down once they are satisfied with the set of statuses.
To your question above: Yes there is a way to add new statuses to a non-simplified workflow in the workflow-editor. Then on the board they will show up and you can add columns for those new statuses as you like.
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