So I tried to export a map with parcel annotations this morning but initial attempts resulted in a map with no parcel annotations. Whilst labels and annotations were all showing correctly for road centerlines and suburbs, the land parcel annotations just wouldn't show.
Because the other layers were showing correctly, then I knew it wasn't the labelling engine. I identified that it must be something to do with the settings of the parcel annotation layer. I discovered that I had previously set the layer to not display beyond the scale of 1:10,000. The map scale was exactly 1:10,000 and was displaying in layout view.
When I made the layer show at all scales, the map annotations displayed correctly in the exported PDF.
Something to remind myself next time: check map scale and display options as it will affect export settings despite what is visible in ArcMap.
I also toyed with the idea of presenting the map with a darker theme, but it probably uses a lot of ink.