Hey Mike- Jeff's gf Jess here...
I disagree about the bread. Make it yourself. A bag of whole wheat flour, dry yeast and some flax seed or wheat germ will only run you about $10. And with that you'll get approx 20 loafs of high quality food. To mitigate the cost of the electric while you're are baking, put a casserole in there too.
Easy/cheep cooking-can of tuna, cooked pasta, can of cream of whatever soup, cheese and frozen veggies of your choice. Should net you a meal for at least 4, or two days of eating. Freeze what you don't eat and have a quick meal for another day.
www.couponmom.com has a great system that shows the local deals on groceries in your area and keeps track of past coupons for reference. Get the Sunday paper and watch all the store ads closely. Don't get sucked into the bogo on meats that BiLo often has. The price is usually inflated to cover the cost of the "free" items. If you like chicken, go for the boneless/skinless breast frozen in the bags. The best price I have seen is about $1.59/lb. Also look for the whole firers on sale, should be about $.59-.79/lb and will be good for a couple of meals and soup stock as well.
If you have the option, buy in bulk. Places like Sam's and BJ's have consistent prices on meat and they don't skimp on quality. Try finding a whole pork loin. The last one we got was about $17 and got cut up and we ended up with 5 meals (for a family of 4) out of it. Beautiful chops and tenderloin. As you cut it up, use whatever marinade you like in the zip lock bag and freeze. When it thaws your ready to go.
The other thing I will suggest is taking inventory of what you have in the pantry right now. Its easy to stock up when stuff is on sale, but if you already have mass amounts or you don't use it, it's just a waste. Good housekeeping will have some good home economizing tips as well.
Good luck to you.