While I was planning an actual calendar, with assigned meals each day of the month, (and I actually had a pretty good rotation going as far as splitting up 6 chicken days lol) you don't always know in advance what you want to eat, or how you are feeling and how long you want to cook.
So I printed & boxed all of my recipes and I will have the kids pull the meal out the night before, if it is something I am not up for, we will repick.
The few meals that are the exemption to this "pick at random planning", especially if you are doing a one time shopping haul-is the stuff that needs to be eaten fresh. In this case, I will make the Italian grill cheese sandwiches with the garlic breadsticks on day one, a nice easy quick meal while I am sorting and putting away all of the groceries. Day two, will possibly be the stuffed cabbage rolls- to avoid the fresh cabbage spoiling, and then the pinwheel steaks with the spinach on day 3. Everything else that requires peppers, onions, garlic, etc. I have previously peeled, chopped/diced onions and peppers in single containers and froze them, so that I just have to throw them in the pot on cooking day. (you can also buy them frozen buy the bag and just pull out what you need)
I took one day to go through all of the recipes and sort out how many pounds of hamburg I would need, how many pieces of chicken etc, and I ballparked a number of $228.00 for everything I had on the list, so I would say $250.00 to be sure. That's a whole month of freshly prepaired, home cooked meals, with leftovers for about $200.00 a month. (because some items such as throw away pans, cooking spray, tin foil etc don't really count into the food total. as well as I factored in some items such as sauces and spices that I already have and don't need to buy.) PLUS some of the recipes are multiple day recipes, like the traditional Italian meatball recipe is for 50-60 2inch meatballs, or more if smaller. you can pull out 20 for dinner and freeze 40 for two more meals, or put away meatballs for appetizers or pizza toppings! (or divide the total to make only what you need and save some $$ there too)
HINT: if you make on bulk shopping list, that lists everything you could possibly ever buy at the market, you can laminate it or put it in a sheet protector and use a highlighter dry erase board to fill in how much you need, or erase what you already have, and you can reuse the same shopping list each month.