Johndaigler, thanks for the resource references. I ended up going it alone (with assistance available from an experienced Cubmaster, who did "Your Flag" for me), and it seemed to go OK. This particular Achievement requires some serious follow-up at home, and all parents were in agreement that it was important to discuss with our boys in more depth as a family. I feel much better now!
Thanks again - I appreciate the time you took to reply, and I'll check out the sites you've mentioned for future reference and my own family's discussion.