Rob, you've got a nice and pretty leisurely canoe trip ahead of you given the five rest days built into the schedule.
My bro and I have done the stretch from Kenoji Lake down to Smoothrock Lake a couple of times in the past five years, once with a take-out at the south end of Little Caribou Lake and the other time at Collins via the Boiling Sand River. Your Onamakawash Lake take-out is yet another of the many options. You'll be waiting for a VIA train that can be anything from a bit early to very late!

There is a nice campsite on the south side of Oliver Lake which is marked in the Wabakimi Project map. On our way to Whitewater we stayed to the left and went down the left channel. It was early September so the water level was a bit low. There was one set of rapids that we lined and ran to get to the lake.
When you get to Whitewater Lake there are two things you want to check out - the Ogoki Lodge complex and the Beckwith Cabins. See this post of mine for some background on both of these interesting Wabakimi stories -
http://wp.me/p25mXk-bKWe ended up camping on the south end of Best island on a beautiful beach that ended up being the buggiest campsite ever - sandfly central! There is a camping area by the Beckwith cabins that might make a better option.
Getting from McKinley Bay into Smoothrock Lake's Lonebreast Bay will involve a few portages but I don't really recall them being all that bad - except for the very first one which we had trouble finding at the end of McKinley Bay.

As you go down Lonebreast there are not a lot of good campsites until you get to an island named Bussey. I think the name comes from a plaque that friends of whoever Bussey was left in his memory on the island.
After Bussey it is a nice paddle down to Smoothrock central. We picked a nice island campsite there before we headed down the west arm of Smoothrock the next day. You will notice some fishing boat traffic on Smoothrock. If you're looking to do some socializing you might instead head down the main stretch of the lake to the fishing outpost.
See this link for some info on the fishing camp -
http://www.thunderhook.com/smoothrock-camp/While you're paddling in Wabakimi Country we'll be paddling in your back yard down the Steel. We're looking forward to it - your maps certainly made planning the trip a whole lot easier!