The way the search works is that there should be a results page that displays all the information using a loop. You would search on the category column of the database and then you'd have multiple records returned in your recordset. Then you would display the information you want by looping and stepping through the recordset. You'd want to check if the recordset is at the last record to stop looping.
If you have multiple uploads set up, you will have to insert the details for each of those uploads. So for each upload you will need one insert. If you have one Digital File Pro upload that inserts more than one image in one upload, you would use a single insert to insert the information into the same row in the database.