Certain pdf documents do not export properly with annotations made in Squid. Squid support has advised this is due to variations in how the original pdf was created (content vs annotation). I hope future versions will allow for reliable export of pdf regardless of the original source pdf.
It appears that some parts of the first page are added to the PDF as an annotation (rather than PDF content). Since we add your writing to a PDF as content, this means that it'll appear underneath any PDF annotations, which is why you can't see any writing on the first page. We would like to add additional options to export in the future to help work around issues like this, but it's not something we have at the moment.
Thanks for creating this feature request. We were happy to help you figure out a workaround and definitely appreciate the value that this feature would hold.
For anyone with a similar problem, if you are importing a PDF into Squid that may have annotations added (e.g. a logo, electronically-filled forms, etc), please "Print to PDF" the document and then import it into Squid. This should remove the annotations (by revising them into PDF content) and will allow you to export/print correctly. We are very sorry for this inconvenience and we will work on figuring out a way around this!