As outlined in the link to another thread about buying a first boat; first you -need to define what you want to do with the boat. Is it day use, fishing, taking kids tubing, wake boarding or water skiing? Do you want to spend nights on board the boat? Do you want to spend weekends in the boat, or do you want to spend weeks at a time? What part of the world do you live in. How big is the family and will they enjoy boating--what type of boating? The C Dory is sort of like the VW camper of boating.
Also key is to define your budget for purchase and maintenance.
David Gerr'sThe Nature of Boats does go into basic boat design and type. I think it is a great reference book. However, it is technical.
Chapman's gives you information on how to run a boat--but not a lot about boat selection. I refer to both of these books on occasion and they are great reading for new boaters.
An older book: Boating Magazine's Insider's Guide to Buying a Powerboat: Featuring Tips and Traps for the Smart Boat Buyer Paperback by Robert Lamy is another place to start.
Also Buyers' Guide to Outboard BoatsSelecting and Evaluating New and Used Boats by David Pascoe. David Pascoe is a semi retired marine surveyor, who can be a bit controversial, but all in all he is very thought provoking and does give a lot of general information on what to look for in buying a boat.
Certainly reading Bill and El's adventures will whet your appetite.
The classic C Dory book is "River Horse" by William Least Heat Moon--the story of taking a C Dory coast to coast with only a few hundred miles of portaging. Consider that Mr Moon is not an experienced sailor--and there are some "interesting" comments on the C Dory.
Of course the book which everyone should read in their lives--and hopefully your have already read it is Wind in the Willows by Kenneth Grahame . It is a children's book, but with a number of wonderful lessons of life in it:
“Believe me, my young friend, there is nothing - absolutely nothing - half so much worth doing as simply messing about in boats.”