Mendix Document templates have only limited support for styling and visibility. The easiest way to reproduce the same page in a PDF format is to use the templator module https://www.notion.so/gajduk/Templator-d35db3ba165346e3b243d6695636ccd4
With this module you can use the same exact page and generate a PDF from it. No need for a separate template and all the widgets and visibility settings will work out of the box
Check box widget cannot be used in document template, you can only use dynamic text. Hence, it shows as text (yes/no).
Based on you comment, I assume you mean you want to only show the objects in the data grid where the value is yes. If that is the case then you can add a data source microflow, in the microflow retrieve required objects from database and pass out the list.
Hope this helps!