Do they not teach home ec anymore? I am probably functioning from the advantage of being a foodie who was taken under the wing of a very frugal member of the Greatest Generation (that would be my Grandma, my personal Lord and Savior) and my Mom, who taught me a damn lot about running a kitchen, too.
I think your biggest mistake (besides the “bag of white chicken meat”) was buying a tomato in Chicago in January (A buck fifty?! Faith and begorrah!). I live in SoCal and am lucky enough to have great produce all year round (and great Mexican food for, yes, under $5), but it still pays to buy in season. The big tipoff: the cheaper the produce, the better. Also, ethnic markets tend to be cheaper. Also groceries that cater to the working class. If you’re going to a pretty grocery store, filled with the augmented and chemically processed upper crusties, that prettiness will be reflected in the price of the food. Shy away from places filled with idle housewives during the week and go to places that are packed on Saturday with families.
Also beware that prepackaged food is going to translate into you paying for that preparation and packaging. You will pay for convenience. I buy whole things as often as possible and prepare them myself. If I’m making a stir fry during the week for example, I will use some of my chore time on the weekend slicing onion, bok choy, deboning and skinning a few chicken breasts, or whatever, and storing it in the fridge so I can throw it in the wok at the end of a busy day. (Gladware is a savior for keeping prepared veggies and such in the fridge). I typically plan meals 1-2 weeks ahead. I spent part of Saturday taking apart four chickens, dicing a bunch of vegetables, and preparing a few marinades.
A chart of what is in season for Illinois is here [PDF]. Even better is if you can buy into a co-op, where a local farmer will box up a week-months worth of seasonal veggies on the cheap. Learning how to use them is a challenge, but I bet a guy like you could figure it out with a little practice and some help from culinary websites such as www.recipezaar.com or order a copy of The Joy of Cooking, or the Better Homes and Gardens cookbook. Not to mention CS, where you can ask one food question and get 100 food answers, and most of them right to some degree.
You have to have staples on hand and have a certain knack for putting them together to make it all work. A bit of what I have on hand at all times:
A case each of:
Tomato paste, crushed tomatoes, diced tomatoes, tomato sauce
Russet potatoes
Onions
Garlic
Rice (I’m a foodie so about 5 types)
A big bag of pinto beans
Lentils
Barley
Corn meal
Corn starch
Flour
Sugar
Concentrated lemon juice
Shortening
Butter
Olive oil (on the cheap from Trader Joe’s)
Bouillon cubes for chicken and beef
etc.
When I buy chicken I buy whole chickens and section them myself. Much like a cow, I find that different parts of the chicken lend themselves to different cooking techniques. I prefer thighs stewed, while I adore grilled legs and wings and baked breasts. Backs and necks get saved for stock. For a small amount of money (stock is mostly made from what would in an American diet be wasted) and time (12 hours of low low cooking) you can transform the lowliest meal into something entirely grand.
Some of this you either have to be raised knowing or you have to get a brain about it. Example: Beef “stew meat”. The biggest joke in the meat section. Go to the butcher and buy “top round”, or what some people mistakenly refer to as “London broil”. About a quarter of one will braise up nicely for two people and a whole one will cost 6-7 bux. I buy two whole top rounds at a time and section them for storage in the freezer. This cut also has the advantage of being quite lean (hence the need to braise), especially if it has been trimmed down.
Ground beef is also frozen into varying portions, from .5-2lbs. Invest in some freezer bags and an institutional size roll of plastic wrap. If you have the freezer space, also invest in a scale and form .25lb patties individually wrapped in plastic wrap for quick and easy burgers.
Ass broke and don’t know what to eat? Hit the meat section and look for: smoked ham hocks, salt pork, smoked pork neck bones, a smoked turkey leg or even bacon. Sort through some pintos and simmer all day in a pot with your smokey meat product of choice. Salt generously when tender. Serve with rice, cornbread, or corn tortillas to complete your protein. You can eat it for days, and even re-fry them the next day and have burritos or bean tostadas or whatever. I keep hearing that Chicago has a burgeoning Mexican and Latino population - if so you should be able to find a tortilleria serving up fresh and awesome corn tortillas made daily on the cheap. Way cheaper than that “taco kit” and the tortillas will keep quite a while in the fridge, to boot.
I blow a lot of money on my herbs and spices (because this is also my hobby), but say you had to buy some bay leaves, at minimum: $2 in the Mexican section of the grocery. It’s like setting up house: you have to go out and get a couch and some dishes and shit like that, but once it’s done it’s done (well, you have to go out and get new staples periodically, but a well-stocked pantry is your friend.)
Seriously, I feed four adults for $500 a month, and we eat really well. Of course if you don’t want to put the effort into learning how to cook, and investing in gear and whatnot, then continue to eat out. But I find that dining out thins out my wallet and thickens my waist. Not to mention very few places prepare food better than I can at the price I can. Plus I have the advantage of knowing exactly what I put into what I eat, which is important in these high-fructose corn syrup, peanut allergy, and trans-fat times.
I know this is sounds like a lot - and it is. It takes effort. Like any practical aspect of life, it takes practice and elbow grease and time. But, like learning how to balance your checkbook and play the FICO/credit reporting game, the payoff is worth it.