for the moment, in this special case for the caleb export, I recommend this:
in the dialog, where the user selects what type of data to export, add a text box for defining the sender email address, which you use as the From: address when sending the email to Caleb. That way the user will get the reply from Caleb.
On the server side, we have to setup just one email account that knows a proper SMTP server or Exchange. That is done only once, either by the installer or by the System administrator.
For a proper solution to the problem of sending emails, we need to look at later when it becomes more urgent.