Thanks for the input Ingo! I'll definitely take that into consideration. I was debating which direction to head once I arrive, heading North from Rock Harbor getting the tough portage out of the way from the start, and staying at Duncan Bay or Duncan Narrows (whichever is coolest) the first night, was my original idea.
Which direction is a toss up, and I could make arguments either way. Do you know which boat you're coming on? The Ranger III can drop you off at Mott Island and you can easily get to Caribou, Moskey, and on a good day Chippewa, on the first night.
1st night @ Duncan Bay or Narrows (from Rock Harbor).
Go whichever way the wind is blowing

.
2nd night @ Belle Isle.
My favorite!
3rd; Pickerel Cove.
Consider staying at Belle Isle and day paddling, esp if weather allows you to get out to Amygdaloid.
4th; McCargoe Cove.
Consider going on to Chickenbone to make the next day shorter.
5th; Lake Richie Canoe.
This was a longer day for us from McCargoe, but totally doable. Just tired.
6th; Malone Bay or Wood Lake (depending on how Siskiwit Lake treats us, strong Eastward winds and forget it)
I'd just do Wood Lake, unless you just really want to do Malone Bay (it's on my list because I haven't stayed there).
7th; Lake Whittlesey or Chippewa Harbor (or both!)
Can't go wrong.
8th; Moskey Basin (from Chippewa Harbor....!?!)
ugghhh... get going early and take your time.
or if weather permits (rare, I'm aware), Chippewa Harbor to Caribou Island (avoiding the mouth of Conglomerate Bay.
That would be nice

, but be careful!
9th; Moskey Basin or Caribou Island [pending weather and/or zero day(s)]
If you come through Richie, you won't want to go any further once you're done with the portage. It's a short paddle from the portage to the campground.
10th; Tooker Island
11th; Rock Harbor
The 2 account for a weather day, which is good.
Question: Portaging from McCargoe Cove to Chickenbone Lake; the map I'm currently using isn't quite clear on where exactly I'm suppose to exit the portage trail and enter the water into Chickenbone Lake..? I am somewhat familiar with that portion of Indian Portage Trail, but I've always hiked it North, from W. Chickenbone Campsite. If memory serves me right, once close to McCargoe Cove the water passage thins drastically with thick vegitation. I remember the loons' nesting area in there and I also remember a beaver dam. How long of a portage is McCargoe to Chickenbone Lake approximately? Will it be one of those things where it will make sense once I'm there or is it common for people to get turned around in there?
It will make sense. The put-in is right at the end of Chickenbone. It's been a few years, but I don't remember any ambiguity.
Normally I'd recommend building in a weather day or 2, but you have enough time with short enough days that you can make up whatever you may lose. Still jealous

!