Travis, I haven't read every reply on your thread, but I want to quickly share some thoughts before I head out the door for work.
It looks like you're spending around $900/month to feed your family. My monthly grocery budget is $500, and that includes food for three large dogs and six cats. If it was just humans (2 adults and 2 children), we could definitely cut that back to $400/month, possibly less. This is in a cold part of Canada, where milk costs around $6/gallon, and most of our fruit and veg is imported, especially in the winter months (October-April). Typical prices would be $0.80 for a pound of bananas, $1.50 for a large can of beans, and $5 for a pound of butter. Ground beef, on sale in bulk packages, runs around $3/pound. Apples are usually around $1.50-2/pound, and grapes run around $4/pound and up.
We do grow a big garden, but I don't think it saves us much money, as the things that grow the best here are also very cheap to buy at the store. We keep chickens for eggs, and that saves us a bit of money, but again, not a ton, as eggs are usually pretty cheap.
We do cook most of what we eat, from scratch. We also eat seasonally, buying the fruit and vegetables that are in season, and therefore cheap, and using that as the starting point for our recipes. Right now, it's apples, oranges, squash, and root veggies, for the most part. In the spring, it's asparagus and strawberries and eggs.
We don't eat a ton of meat. I normally buy less than 5 lbs of meat per week for the whole family - usually more like 3 pounds per week, though when turkeys and ham are on sale around holidays, I stock up. Some weeks, we don't eat meat at all. We do eat quite a bit of dairy, and eggs.
We buy dry goods in bulk quantities when we can - rolled oats, flour, sugar, rice, and such we buy in the largest bags we can. Usually 20+ pounds.
I think that if you really want to reduce your grocery budget, you need to start with changing what you are buying, rather than trying to grow your food. If you struggle to find time to cook, gardening is not going to work out well. Plus, you can invest a lot of time and money into a garden, only to have weather or bugs wipe out your crop.
I will say that not every meal needs to be gourmet. In fact, you'll find the whole thing a lot easier if you plan to eat a lot of 'peasant food' - things that take one or two pots to make, produce large amounts of leftovers, and preferably don't use up too much meat. Favorite meals around here include chili, pasta with meat sauce (though the meat is often stretched with zucchini), soup, and roasted root vegetables. We also do lots of Mexican-style burrito meals (beans + corn + squash; meat optional, though it's great for using up leftover chicken or turkey), Indian-style lentil meals, and Thai and Chinese style stir-fry meals. Leftovers are a life-saver - we only cook about 4-5 days a week. Lunches are sandwiches or leftovers (I take leftovers to work), and breakfast is porridge (dressed up with applesauce or raisins and cream), toast, or yogurt and fruit.
We don't feel 'deprived' at all with the diet we have. It's really quite healthy, not terribly expensive, and even the cooking isn't very time-consuming.
Having said ALL that, only you can decide what is going to work for your family. It takes a lot of commitment to change how you eat, and if you view it in the negative (spending less money), you'll probably find it quite difficult, because everyone is going to feel like it's a deprivation. Even viewing it in a positive light (we're going to eat healthy, seasonal, home-cooked food), it may be a big change, and not easy. Anyone who doesn't already know hoe to cook from scratch will have a steep learning curve, both in the cooking and in the meal planning, as most cookbooks highlight fancy meals that take a lot of prep work, rather than basic food that is quick to prepare. Personally, I believe it's worth it, though.