I’m having no luck exporting a pdf from Layout. When I try to export I get a “Problem Encountered” box
“There was a problem exporting to this file.”
I’ve tried exporting to my desktop and my usual drive on the local office server.
This is frustrating.
Several possible issues. First could be due to incorrect installation of SketchUp and LayOut. Did you install them by right clicking on the installer and choose Run as administrator?
Another possible thing could be something simple like a bad dimension or an inserted image.
If that’s the case and the LO project is a multi-page thing, try exporting one page at a time and see if the export is successful except for one page. Then start deleting things on that page until it will export successfully. I’ve done that on some files others have sent to me and have tracked down the problem entity and replaced it which fixed the problem.
If you can share the LO file I’ll try to find it.
So, after giving it some thought I found a work around:
I exported .jpgs and then used adobe acrobat to group them into a single pdf.
Thanks DaveR… I’ll try reinstalling. You are very generous. But since I did the work around, I’ll leave it at that for now. 
I guess if the .jpgs give you satisfactory quality that’s good.
Find the downloaded installer or go to sketchup.com/download/all and download the latest one. If, after clicking on Run as administrator you are presented with options, select Repair.