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You can learn more about the Import Data App here: http://www.jotform.com/help/308-Import-App-Easily-import-your-Excel-or-CSV-data-into-JotForm.
Unfortunately, if you inserted a picture or image to the excel or CSV file, it will not be imported, there's a template that you need to follow so that the data will be imported correctly.
What might be possible is allowing direct links of the files or images then add them on a specific column in the excel/CSV spreadsheet. Right now, it is not supported but I can forward it as a feature request.
Here's an example, this is my form: http://form.jotformpro.com/form/51449292003955. It has a "File Upload" field.
This is the Import Data App, you'll see that there's no dedicated template or format for the File Upload field.
Do let us know if my assumptions are correct and if this is something useful for you in the future.
We'll wait for your response.