I think your major problem is going “gluten free!” instead of simply cutting out the gluten. That is, you’re buying analogs to the old gluten-containing foods, instead of reworking the underlying framework.
Now, in some cases, that’s kind of desirable. Sometimes, you just want a cookie, dammit. In a lot of cases, though, you can greatly increase the nutritional profile of your meal, without increasing the cost (or at least not increasing it by as much as going with the “gluten free!” substitutes, since you are talking about replacing what is essentially the cheapest of the cheap staples with…anything else).
Oatmeal for breakfast? Bagels for lunch? Bread? Pasta? Granola bars? They’re all out there. The bad news is that everything is smaller and more expensive than its traditional counterpart.
While you can just do that, the other option is to simply forego them altogether. Swap the oatmeal for an omelet with your favorite veggies, and now you’re running on protein, higher-quality fiber, and good fats, probably for cheaper than that oatmeal.
Nearly everything can be wrapped in lettuce or turned into a salad. Pasta can be replaced in most cases by things like spaghetti squash, which can also be made into new hit dishes like this cheesy casserole (which never lasts long at any party I’ve taken it to, and doesn’t require the “exotic” ingredients this blogger used; you pretty much can’t go wrong with any kind of cheeses you have on hand).
If you really want to stick with American cuisine, add about three dollars to the cost of your meal for GF pasta, pizza or a hamburger bun.
In the case of the pizza and pasta, if you’re going to go for analogues, you don’t have much choice, you’re right. This is one of those areas where I’ve simply changed my “food framework” and ditch them altogether, in favor of salads and higher quality meat/vegetable-centered dishes (lamb chops at an Italian restaurant, for example).
On the hamburger front, though, you could spend that couple of extra dollars for a “gluten free!” bun, which is likely going to fall apart on you by about halfway through your burger, or have the taste and texture of cardboard.
Or…you could save the money and get it lettuce wrapped.
While it’s still hit or miss at places where burgers aren’t their staple items, “burger joints” (Five Guys, Red Robin, etc) won’t bat an eye at the request and their idea of “lettuce wrap” is about half a head (as opposed to a single piece for each side), at no extra charge. In fact, Five Guys will simply ask you one question — allergy or preference? (They take a few extra steps to minimize cross contamination if it’s an allergy.) I’ve actually come to prefer my burgers lettuce wrapped, because the flavors of the burger don’t get soaked up into the bread.
I highly recommend checking out the Paleo and low-carb friendly gluten/grain free sites, such as I Breathe I’m Hungry, Detoxinista, or Satisfying Eats, among others. While you’ll still find the old favorites, a lot of these sites have re-imagined most of the comfort and go-to foods under new frameworks, looking to make foods that taste good in their own right, as opposed to trying to find “gluten free!” replacements for the things they grew up on — and made them sick.