There are only  two of us, and I do all of the food planning and packing, but Spartan1 plans the route and itinerary (for the most part.)  We have a definite route in mind most years, with layover days planned in, which sometimes become wind-bound days and sometimes are just for the fun of it.  We are definitely "old fogeys" now, but I have never in my life been "bored stiff" (whether in the canoe country or anywhere else) so that isn't a problem.  Finding something interesting to do just is part of my nature, I guess.

Routes have changed from time to time, due to weather, due to health concerns, due to "what do you suppose is up here?" and once or twice just for the hell of it.  The year of the "friendly flies" we actually decided to end one day early--that was a first!  

Because of my husband's insulin dependent diabetes we would never dream of starting out, even in the BW, with only just enough food for the planned number of days.  I always pack enough food for two more days, and am very thankful to be packing it back out again if necessary.  It might very well be a life and death situation for him to not have enough food available if the weather turned very cold or we were injured and had to spend a couple of extra days.  But of course our situation isn't really typical.  Still, I would think anyone on a solo trip would be very foolhardy to only have enough meals packed for the exact planned number of days, unless there are lots of extra snacks in that pack.

Solotripper is right about hydration and keeping the blood sugar on an even keel.  This is very important for anyone, regardless of body weight, level of fitness, or general health.  Good healthy carbs, whole grains, protein, and enough non-caffeinated fluid is essential.  

We pack food in two packs in case something happens to one of them.  I don't decide upon what food we will have on a given day, but usually choose on that day, so I am not as efficient as I should be.  But with only two of us, it isn't as crucial.  If I were planning and fixing meals for a group of eight or nine I would certainly have the meals all bagged together.  In the morning we have a big breakfast unless we are in a real hurry to break camp.  We carry our lunch, which is more "snack-y" in an outside pack pocket.  Snacks are always available, both complex carb snacks and the high-sugar ones for insulin reactions.

We really like eggs in the morning, and have fresh eggs for the first four days usually (unless the weather is terribly hot) and Backpacker's Pantry Denver Omelette after that if time is allowing.  The eggs are in a cardboard store carton, in a paper grocery bag, duct-taped under the stern seat of the canoe, and stay there quite safely during portages unless Spartan1 drops the canoe.  (Then we have a big omelet for supper that night.)

After doing this for 37 years I would think planning would be second nature, but I must confess that occasionally I still forget something or realize I have made a mistake.  So I guess I should spend more time like Jimbo getting everything packed up 'way ahead of time.  I always make lists, but don't assemble things until about 3-4 days before departure from Michigan.

We normally have a short last day, spend some time in Ely or Grand Marais, stay overnight, and take a few leisurely days getting home.  There are some real advantages to being "old fogeys".    (one of us is retired and the other one gets LOTS of vacation.)

Oh, Tim, I never said I wasn't tough!  Just because I don't want to take a hurried pace doesn't mean I am not tough! 

And I also have a list on the computer which I print each year, keep handy, and check off quite religiously.  Where the rub comes in is usually the last-minute things we buy up in Minnesota, or the thing that I am sure I have packed, but somehow I checked it off without actually putting it in.  Not gonna call that a senior moment yet, though. 

Breakfast type meals get packed together, dinner type gets packed together. Desserts... Breading in a bag of it's own... the second half my lunch & snacks scattered about in nooks and crannies. On group trips, lunch was always strictly up to individuals (per canoe to as be with them at all times) and everyone pretty much knew what the meal portion sizes would be so they could adjust with what they brought for lunch. Group cooler for group food.

One thing I learned to do the first night was physically show everyone how much stuff like dish soap there was and how much syrup we had for x number of pancake meals. Things like that. This tradition started on the trip we discovered one guy preferred pancake soup and coffee flavored maple syrup. His wife used half of the dish soap cleaning dishes for one meal. (They both thought there were similar sized containers for each meal.)

Lunch for breakfast, dinner for lunch and breakfast for dinner, whatever, depending on mood, situation and conditions. What's been hardest for me to adjust is that I need less food in Aug than May. I started with the usual extra 'just in case' meal which always came home. If I do a ten day trip this Summer, I'm only bringing food for eight. There's always plenty o' fish in Aug.

When we started out, we'd shop together for group food friday after work and toss in whatever, in it's original packaging no less, and hit the road hopefully before midnight. That system needed to be and was refined year after year until my first few solos where I was truly anal about what I brought and how it was packed. Lately, since I still use the same food/cook pack that works nicely for two I have absolutely no qualms about tossing in a bag of doritos and/or brussles or some other fragile, highly breakable type food I'd have poo-pooed or at least been disappointed by years ago. Why? Perhaps simply 'cause now I can and have only myself to blame.

On itineraries.
For group loops I found it was advantageous to nudge people along until we pasted the point of no return. It never failed that day three someone would say: "This is a nice place. Let's just stay here." And I'll admit it's tough to argue with someone when you and everyone can easily understand their logic.

Solo, I leave a map with my wife with a line or two and lots of circles and arrows and go over it with a friend that knows me and knows the Park better than my wife. It's sort of a plan full of possibilities and it all depends on what I find and the weather I get. If I say I'll meet you this lake on this day I'll make it a point to be there but beyond that, a day's distance, campsites, day-trips... it mostly depends on wind and clouds although I rarely deviate from the map I leave and even then only if a reasonable person would do the same based on water levels or outright closures.

It's the only place a wear a watch. One day last trip, my first choice for the night already had two groups nearby. The next desirable lake already had one group and I got a bad vibe. It was nice to know for sure that there was enough daylight left to get past an area normally expected to be congested with enough time to settle in and get comfy a lake or two later. Moving five miles or even two on a layover lake - fine by me.

I pretty much do as others have said here, with a large zip-lock for each dinner meal and all its necessary components all together so no hunting in all the packs for the ingredients at dinner time.  I have a separate lunch pack with the cheese, salami, crackers for the day, etc. so I just have to pull that out of the kayak when I stop for lunch.  With a group I make each person buy the snacks, trail mix, drink mixes, jerky etc. for themselves.  That way they each can bring what they want and since it tends to be expensive stuff, it keeps the general grocery bill for a group down.  They each have a small back pack for their stuff and we throw it all in a big pack to hang at night.
Last year we ate well and I think the general groceries ran about $7.00 per person per day. 
Regarding getting to Boulder Bay from Moose Landing North in one day, in mid-summer, may not be possible with a group.  Keep in mind it is busy on that route and may be hard to get a campsite if you do not stop fairly early in the day.  Between keeping your group organized and waiting on others at portages, the portages are a slow process.