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I am an avid cookbook collector and I have done a ton of research for the best books out there for various specialties!
For bread machine breadmaking I recommend the Bread Lover's Bread Machine Cookbook I LOOOOVE this one, I have made many recipes from here, not all of them bake in the machine though, but the dough can be made by the machine.
For traditional breadmaking I have heard great things about this one: The Bread Baker's Apprentice: Mastering the Art of Extraordinary Bread by Peter Reinhart.
And this one: Crust & Crumb: Master Formulas for Serious Bread Bakers by the same author. I am hoping to get both these books once I also take my bread making to the "next level."
Oh my goodness! What a hard question...
For bread machine cooking, I like the rather uncreatively titled "Bread Machines" by Jennie Shapter.
I also like the small book "Flavored Breads" by Linda Colister and my new addition"Beatiful Breads & Fabulous Fillings" by Margaux Sky. That one has mostly "filled" breads, which I'd never tried before.
Oh, yes, and the delightful "Breaking Bread" with Father Dominic. I used to LOVE his series on PBS!
Kindof depends on the bread you are planning and what your family will eat. My bf is far more adventurous and willing to try new stuff than my sisters' families. My sisters and I (seperate households) make a lot of homemade bread and our favorites are:
It's a tie between The Complete Guide to Bread Machine Baking by Better Homes and Gardens and Breaking Bread with Father Dominic. I have not yet decided on a 'best' book for artisian type breads.