https://community.quicken.com/discussion/7867159/faq-how-do-i-post-a-screenshot-in-the-community-from-windows
https://community.quicken.com/discussion/7663259/faq-how-do-i-post-a-screenshot-in-the-community-from-a-mac
Please save images to files of file type PNG, JPG, or GIF only. They're easier to work with than PDF files.
If you haven't done so already, I'd say it's time to call Quicken Support on the phone and request help. Let them do a screen share session with you to review the situation on your computer, to determine the nature of the problem and to figure out how to fix it.
Quicken Support: