To create and email a PDF with no extra prompts, follow these steps:

1. Create a Win2PDF printer for the auto email feature. To do this, run "Add Win2PDF Printer" from "Start -> All Programs -> Win2PDF" and name it something like "Win2PDF Auto Email". 
2. Download and run the free Win2PDF Mail Helper add-on:
   http://helpdesk.win2pdf.com/index.php?/Knowledgebase/Article/View/189/15/win2pdf-mail-helper-download
3. Configure the Win2PDF Mail Helper with your SMTP server:
   http://www.win2pdf.com/doc/index.html?configure-win2pdf-mail-helper.htm
4. Print to the new Win2PDF printer that you created in step 1, and enable the Auto-name feature to prevent the file save window from popping up:
   http://www.win2pdf.com/doc/index.html?pdf-auto-name-files.htm
5. In the File Save window, check "Send file" and optionally "Delete after sending".
6. In the Win2PDF Mail Helper, check the "Auto-send email" checkbox before clicking send. This will use the same email address for all future emails.