After the Messier Objects & Caldwell Objects, Stephen O'Meara has done 3 additional books in his Deep Sky companion series : The Secret Deep; Hidden Treasures; Southern Gems. Each book has 109 objects (plus a few extra). Sadly all seem to be out of print but the Messier and Caldwell books are easy enough to find. O'Meara also wrote book on the Hershel 400. So plenty of objects to choose from. Thus the issue seems to be which are well placed. Stellarium is great, as others have said, and I use the Ocular tool to see how much of the imaging frame an object will fill.
@CharlesBracken has written, "The Astrophotography Planner" available on Amazon. He maintains a database of 109 objects and if you contact him he will do a pdf file for you, based on your latitude and longitude giving the best time of year to image his 109 objects. I believe the personalised pdf costs US$20. (deepskyprimer@gmail.com). He gave a presentation on it to the iTelescope community
https://www.youtube.com/watch?v=MdeZdu6GXoAwhere he lays out his criteria.. moon phase, elevation and number of potential imaging hours in a night.