Sounds pretty good. Windigo to South Desor at 11.6 miles will be your longest hike, but the trail is quite smooth and the uphill portions are not bad. I would opt for a pickup at Chippewa Harbor rather than Daisy Farm as Chippewa is a lot nicer. However, if you want more Greenstone Ridge hiking, then Daisy Farm would be an OK destination. If it were me I would probably spend that extra day at Chippewa Harbor as well, although from West Chickenbone you can day hike to McCargo Cove or Lake Richie. IMO a rest day is better than a tight itinerary, especially since the Voyager only makes intermediate stops if scheduled in advance, so if you plan on Rock Harbor, you will HAVE to make it there regardless of blisters, rain, etc.
re: wife's first real backpacking trip:
1) bad experience = LAST real backpacking trip (potentially)
2) boots need to be well broken in or else the feet will be broken in
3) make sure the pack is properly adjusted
4) take your time; this late in the season you don't have to worry about the campgrounds filling up so if it takes from 9 to 5 to go 8 miles, so what - travel at a comfortable pace, take breaks, enjoy the Island.
Any more questions, please post!
Bob
[edit] Forgot one thing: we went in October for a few years in a row and discovered 2 truths:
1) it can get cold, as in ice in the water bottles in the morning cold
2) it gets dark very early and sitting around in the cold with no campfire (at the inland campgrounds) is not fun, so take headlamps, batteries, and cards/books.