This may belong in Feature request, but then I could be missing something and just not exporting correctly. 
Not sure if it’s possible but it would be great to have watermarks show when 2D exporting directly from SU to a PDF. It shows up when 2D exporting to a JPG but the image is much cleaner looking in PDF. (Raster vs Vector I suppose) Is there a way to get watermarks to show up in a PDF??
Yes, it is a raster/vector issue. The SketchUp PDF/EPS exporter is a vector-only exporter, intended to be used when transferring content from Sketchup to illustration applications like Illustrator, CorelDraw or Inkscape. You can get watermarks to show by printing to a PDF printer or taking the model to LayOut, setting its view there to use Hybrid rendering and exporting to PDF from there, preferably without Jpg compression.
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Thank you I knew there was a way around it… I was hoping to avoid LO but I need to embrace it.