I'm always amazed at how many meals some get out of their rotisserie chickens. They must be HUGE chickens! My family of 2 (sometimes 3 depending if DD is home for dinner that night) can maybe get 2 meals out of them. The ones I buy must be small in comparison.
We don't buy them anymore because we have moved to a no processed mostly plant based diet but when we did, my family of 3 would eat only the breast by itself. Dinner one was sliced chicken breast with sides. Usually this left a small amount of breast that I would add to a Caesar salad for dinner 2- with whole grain pasta thrown in it was a filling meal. Each leg quarter would be stripped and saved to use in a variety of ways- Chicken noodle or tortilla soup, sour cream chicken enchiladas, chicken pot pie.
To the OP, I also think that amount of cut is ambitious and would choose to work an extra day or two a month to save for vacation however I will make a few suggestions. I stock up when HEB has a good price on something but my main tip is to cook from scratch and cut down on meat.
We have salmon once a week. All other meals are plant based except for special occasions and maybe once a month I'll make an old favorite beef or chicken dish.
This week for instance-
Wednesday- New Years Day so we had our traditional Crab Legs with twice baked potatoes, asparagus, black eyed pea kale soup.
Thursday- Cauliflower cakes, green beans, salad
Tonight- Black bean nachos - I use Central Market whole grain multiseeded chips
Saturday- DS's birthday so lunch out- We'll all probably have enough leftovers for dinner.
Sunday-Lunch-Whole grain Pasta topped with a fire roasted tomato and spinach sauce
Dinner- Caesar salad
Monday- Salmon, carrots, broccoli, baked potatoes
Tuesday- Caesar Pasta salad
I keep the freezer stocked with single portion leftovers that DH and I eat every day for lunch. Right now we have potato soup, home made whole grain macaroni and cheese with broccoli, black eyed pea Kale soup, black beans and brown rice, and the last of the homemade turkey pot pie from the Thanksgiving leftovers for lunches. DD eats from the freezer once or twice a week and eats out with friends the other days. She pays for lunches out from her allowance and usually only pays maybe twice a week. Once a week they go to the free lunch a church puts on for the high school and usually once a friend with a stay at home mom cooks for them.
The three of us eat breakfast at home. DD usually just greek yogurt with a scoop of peanut butter but sometimes Special K (the one processed cereal that DD can't seem to give up.) DH and I alternate oatmeal with fruit and almonds, Whole grain pancakes, egg sandwiches, omelets, and once in a while whole grain bagels.
Our grocery bill dropped as I cooked more from scratch and bought less prepared processed food and meat. Pasta is about the only processed thing I still buy consistently.