When you use the Auto Send option it just does it, you don't have to press enter. It takes a while, as it still does each one individually, but no user action is required.
 
As for the second page, modifying the RTM seems to make the most sense. FYI, if you want to send the second page with emailed statements but not printed, you may be able to use RTM Groups to automatically choose the form. We use it on Travelers by Item anyways. The way it would work is that you enter a 1-digit code in AR-A, and then save the RTM with the same digit added to the default name, right before the extension.
 
So, if your default RTM is ENARE4.RTM, and you enter an RTM Print Group of "E", save the email one as ENARE4E.RTM. Then you process as normal. I presume you're already using Customer Class to select out which statements to do by email.