Ways to make the cooking routine more efficient

For years I did the 'once a week' cooking, which has the advantage of not requiring much freezer space (which I didn't have, with my under-counter apartment fridge). Part of the trick was cooking something that could be used multiple ways with minimal effort -- a blend of ground beef, onions and peppers could be turned into a pasta sauce, mexican food, etc.

These days, I still don't go quite to the extreme you're talking about, but I will do things like make way more than I know I'm going to use right away, and freeze the rest -- chili, black bean soup, stock, lasagna, etc. When chicken's on sale, I'll poach a large batch, shred it, then freeze it in zip top freezer bags. I can turn it into chicken tacos in a few minutes -- thaw with some water in a pan, add spices, and cook 'til the water's mostly boiled off.

Now, as in the past few months I've made a lot of meals for my brother's family while his wife was pregnant with twins, some considerations:

• containers : you're going to need a lot for a month, especially if you're preparing sides and such. As I had a membership to Restaurant Depot, I was able to get 2 1/4 lb rectangular aluminum containers normally used for carryout packaging. Of course, I had to get a case of 400 ... if you know a restaurant that uses 'em, you might ask if they'll sell you a few dozen. You want something that seals tightly, and you'll want to fill them so there's not much air space left in them.
• labeling : all containers should be marked with what's in them (if you have to open to look, it's not going to last very long), the date it was made, and possibly reheating instructions and/or ingredient lists (see below). My mom would use masking tape to label things, I just got the lids that had paper on one side, aluminum on the other.
• variety : my sister-in-law started getting heartburn from some ingredients (tomatoes, onions), which meant that the items I had made didn't work out so well. (She was fine after the pregnancy, though, and made use of the dinners then).

One thing I've heard about, but never done myself, is people who have a dinner exchange -- sort of like a cookie exchange for the holidays -- everyone makes up a number of casseroles, or whatever, and then people meet up, and everyone takes one of everyone else's items home. So, if you're thinking about doing this, and know of other people who might want to, also, you might be able to get some extra variety. (of course, if you don't like their cooking, it might not work out so well).

... and one last thought -- it won't help on the baby preparation front, but if I were going to do this as a regular thing, I'd consider making one or two recipes, with batches for 4-5 dinners each ... so I was staggering things, and not having to spend a whole day (or weekend) trying to make enough different things to have variety for a whole month.

I came up with a technique one Thanksgiving that I've used for complex meals ever since.

I have three Digital Cooking Thermometer/Timers and a dry-erase board on my refrigerator.

On my dry erase board I draw a table something like this (I don't use the actual headings, they're here for clarity):

Task 1            | Task 2                | Task 3
Baste turkey (60) | Prep green beans (30) | Prep pie (15)
Baste turkey (60) | Prep potatoes (20)    | Turn down oven to 350 (20)
Baste turkey (60) | Cook green beans (10) | Cook potatoes (20)

The numbers in parentheses are the time in minutes. I set each timer to the appropriate time, and cross out each item as I go. The thermometers are positioned directly above each column.

(You can use any timer really, I just like mine to serve two purposes)

It's flexible enough that you can do just about anything this way. You shouldn't feel obliged to use a single column for a specific item, it's unnecessary. Notice that potatoes span columns 2 and 3.

Clearly this requires thorough planning, but your question states that this is assumed.

I had tried other methods where I planned everything meticulously using the wall time (e.g. 4:30 start potatoes, 4:45 start beans, 4:50 baste turkey, 4:55 resume beans) but this was chaos and you will inevitably lag somewhere which means you're having to adjust your times in your head on the fly. Not fun.

Update

I didn't make this clear, but you don't need to set the timer to time exactly how long each task will take to complete. You can (and should) include any appropriate buffer time before the next task needs to begin. e.g. In my example above "prep green beans" would never take 30 minutes, likely just 10, but for the timing of my meal I don't want to start my potatoes until 30 minutes later, hence 30m for the green beans.

I'll sometimes also have a timer set for an "idle" task. (e.g. if I don't need three timers for most of the meal prep, but I'll need three towards the end (dessert), then I may set timer 3 for a 60m "idle" task to let me know when to start dessert) I initially overused idle tasks when starting this out (e.g. Task 2: prep gb (10), idle(20), prep potato (10), idle(10), cook gb (10), ...), but this confused the hell out of me and I had timers going off that had me scrambling to see that the next thing to do was... nothing. That's why I started bundling idle time into the previous task.