Okay, you asked for shopping advice.
First off, you need to shop Whole Foods like you need a hole in the head. Seriously, Whole Paycheck is for the rich and stupid. You can eat healthy at Kroger, possibly even moreso than Whole Foods because Kroger will have less process crap dressed up and marked up to look healthy.
Second, avoid the middle of the grocery store. The outer aisles and sections are where the fresh, unprocessed foods are.
Third, chicken is cheap, healthy and versatile. I buy whole chickens for like $4 & roast them buy rubbing fresh seasonal herbs, salt, pepper, paprika and crushed garlic on and under the skin, then wrapping the bird in cheesecloth soaked in olive oil before baking. From there, I make soups, stocks, sandwiches, broths etc out of it. I roast the carcass bones and boil them with fresh carrots, celery, onion and ginger to make chicken stock that I in turn use for soups and stews. Super simple and you get a ton of mileage out of it.
Shop seasonally. Buy fruits and vegetables that are in season in your area, and you will shop cheaper and healthier than buying frozen, canned or otherwise processed. The produce will taste better because it hasn't been picked unripe, sprayed with agents to fake ripe appearance and shipped up from the southern hemisphere. While the farmer's market is ideal, but not everyone has access to them. Farmer's markets are not necessarily the cheapest deal in town, either.
Do you have any ethnic markets? Those can be a great source of fresh, seasonal produce at cheap prices. I like to to go to them and pick stuff up I've never heard of, then Google recipes.
REJECT RACK. REJECT RACK. REJECT RACK. Or in the parlance of Kroger and its subsidiaries, MANAGER'S SPECIAL. Eagle eyes. Keep them peeled for those orange and yellow manager's special labels, particularly in the meat and seafood aisles. Buy fresh meats, poultry and seafood on manager's special, and PROMPTLY break it down and freeze it for later use. Also, the reject racks will often have stuff like bags of lentils, pearl barley, pastas etc.
Speaking of meat, switch from ground beef to ground turkey.
Switch from sour cream to nonfat Greek yogurt. They are almost identical in taste and texture.
Switch from cream cheese to neufatchel cheese. The latter is 1/3 less fattening, but otherwise indistinguishable. It's sold side-by-side.
Buy staples like flour, sugar, salt, baking powder, cornmeal etc in bulk, and make your own breads and biscuits* instead of opting for canned biscuits or mixes.
*this assumes you have more time than money. Bread baking is an art that requires practice and a lot of time, but worth it. Sooooo worth it in cost and quality. Biscuits are much quicker and easier.