To take an example of an edition that does this really well: the "Landmark" series for Thucydides [1] and Herodotus [2] both qualify as "big, difficult" books, but the book comes with additional secondary sources that aid in the reading to orient the newbie in how to approach the text.
[1] https://www.amazon.com/Landmark-Thucydides-Comprehensive-Gui... [2] https://www.amazon.com/Landmark-Herodotus-Histories-Robert-S...
The indices, maps, and other additional information was a great aid in understanding the text.