I gathered some of my trail books to review and give you a response and I became completely absorbed in looking at hikes for next year. Too soon for that. So, with no notes nor particularly organized thoughts I'll just give you random answers to some of your questions and my opinion on what works for me.

Sorry, I am not familiar with your book. The combination of CD and print sounds very intriguing. Sometimes I carry an entire guide book just for the information on a few trails and it would be much better if I could print just the hikes I'm interested in.

A new edition is warranted when there is significant environmental or political change such as large fires, trail head closures or land use changes. Of course not every rock slide or ranger station closure is cause for an update. Updating a book to add or replace some hikes with others is also a good enough reason for a new edition. Also, nothing wrong with an update just to offer better tools for logistics.

Hikes arranged by geographic area and trail head is a tried and true format. It's easier to read and help me make my own deviations. My Trinity Alps Wilderness guidebook has trail descriptions arranged by paved access roads, which coincides with geographic areas.

Trail difficulty, best season, highlights, hiking time and other subjective points are best dealt with in two different ways in my opinion: either the hikes are listed in tabular format with columns for each issue, usually in the front of the book or those issues are addressed before each individual description. Why not both?

An appendix with options for loops, off trail routes and climbing routes works for me and I understand you could do volumes on each of those topics for the Winds.

Favorite books? Falcon Guide Publishing and Wilderness Press both do an excellent job; they are easy to browse for whatever type of trip I'm looking for at that time. I have two books by Margaret Fuller and I find them more difficult to read. I'm sure all the information is there, but the type is too small, something about the maps is confusing to me, and the technical details need visual separation (tables, bold print, headings and elevation profiles)from the wonderful descriptive narrative.

I add notes to trail descriptions and I would appreciate a blank page at the beginning of each section.

Maps. A general overview map, an overview map at the beginning of each section and a more detailed map for each description. Include a profile of the elevation of each description, showing points of interest. A map showing significant fires over the last 10 years, at least those having a current impact. A list of the quad maps, Forest Service maps and third party maps.

I hope this helps.
Enjoy.