Yes, there will be a second printing. Sign-ups are not yet opened. The exact date is not yet fixed but won't be very far off. I suggest you read the FAQ
in the meantime, that should answer some of your questions.
Dogbeard wrote::pipshrug: Is there a way to sign up for an Email reminder for when/if the next order will begin.
Not that I know of, sorry.
Edit: You could subscribe to this RSS newsfeed: http://book.fallout-equestria.com/forum/feed.php?mode=news
That's what is being shown on the front page of the website and should contain any project related news.