Brent, I totally understand where you are coming from. When I used to work outside of my home, I ended up packing lunch a lot because I love good food. There's only so much fast food or cafe type lunches I could take. Plus I couldn't afford to eat out every day (and it really bugged me that I was paying so much for crappy food!).
I still do some of these things to prep for lunches now because we are a busy family- anything that can be done when things are less hectic really helps when we find ourselves really busy.
We pretty much eat all our food prepared from scratch, and a fairly locavore diet. When I'm making supper, I ask myself if I can prepare more servings now to use in recipes later this week, or as-is for individual leftover portions. I make a wicked meatloaf, double the recipe and cook half in a traditional loaf pan and half in a muffin tin. Remember that if you are cooking full sizes of recipes and serving sizes together in your oven that the individual sized pans will cook in shorter time than a loaf/casserole sized version of the same recipe.
With the meatloaf example, I'd cool the muffin tin, throw it in the freezer, then pop out the "meatloaf muffins" and bag 'em in a large freezer bag. Packing lunch for the next day is as simple as throwing some rice/potatoes (rice can be frozen in serving sizes) and one or two servings of meatloaf in a reuseable container, and taking some carrot sticks/an apple (prep a bunch of carrot sticks and keep in water in the fridge for several days). There are lots of great recipes out there for casseroles and the like that can be made ahead of time and frozen in individual portions. Having lots of choices for condiments and salad dressings/dips can help to make meals more interesting.
My best lunch packing investments have been good quality cooler bags, reuseable freezer blocks, and good quality food-safe containers (I prefer glass, then stainless steel). I take full size cutlery in lunches, if you have a set of matching cutlery and fear losing pieces just buy a cheap set new or used and keep it for lunches. I find that most cooler bags marketed as lunch bags are too small to accomodate even a kids' school lunch if using all reusable containers, so a few years ago we started using the medium-sized zippered cool/warm bags sold as reusable grocery bags at the grocery store. They are cheap as they come and really sturdy. The freezer blocks are found at the dollar store here, and you can find some glass ware.
Depending on your lunch room situation at work, you can even get a cheap set of dishes (used Corningware is great because it's virtually indestructible). I like freezing individual portions of soup and chili in smaller glass bottles. If packed in a lunch bag in the morning with no freezer pack, by lunch it's thawed enough to get out of the bottle and into a bowl to reheat in a microwave. If there's no microwave another great investment is a stainless steel thermos...although a dear price I LOVE my Sigg metro mug for coffee as it really keeps it piping hot for 8 hours or more...$40 but it's been in heavy use for five years now and no signs of stopping. We also have some Thermos vacuum insulated stainless steel 10 oz jars...got 'em at a yardsale never used for cheap.
So, hope my rambling helps inspire. Enjoy eating well and saving your money at the same time.