Checkboxes and radio buttons work a bit different from text boxes and text areas.
To dynamically set the checked state of a radio button or checkbox, you must first statically set the checked value. Then in the Property inspector, click the Dynamic Button.
Click the lightning bolt next to Check IF and select the corresponding recordset column. In the Equal to section enter the checked valuer for that checkbox.
File fields are a bit different, since they are meant to read from the clients computer, they cannot be given a value at page load.
See the "How to apply Digital File Pro to DataAssist Insert and Update pages" tutorial for instructions on how to maintain the file name from the database on update. It is available in the How To section of the Digital File Pro support page: