I would argue these should leave the cursor in the original place. Is this possible?

What do you do about multi-line todo items? Is your solution to just keep all items short? I like to include relevant details to the todo items in the item itself, which seems reasonable. Line wrapping is messy, because it doesn't indent properly. If I break lines manually the highlighting of your plugin breaks (imho).

Could the syntax highlighting be updated to treat text on the same indent level the same as the last todo item?

- parent item
  - child item with really long description so I break it
  onto the next line