Is this regarding uploading PDFs into the media library on an Event Espresso event editor page, or more of a general WordPress usage question? If the former, have you tried uploading the PDF in WordPress > Media > Add New?
With regards to screenshots, usually it just works to upload a screenshot to your site’s WordPress media library, then you can post the URL to the screenshot in a forum reply here.
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Support forum for Event Espresso 3 and Event Espresso 4.