I agree with RUTH that Fitday can help you with this issue and I also have a Diabetic Cookbook (by the same name) that has some recipes and the nutritional info with the recipes, so they are available. You can also GOOGLE lots of Diabetic recipes online as well.
I find that the portion-based plan easier to follow for breakfast and lunch, but for dinner, it can get more complicated as you stated -- especially for prepared meals like chili or shepherd's pie and so forth. More manufacturers are putting diabetic info on their foods than before though ... but it's the homemade stuff you need a little help with.
When I make a meal, I count the servings ahead of time as I am making the dish; meaning, I carefully measure the right portions per person as I am making up the dish and/or serving it. For instance, when I could pasta, I measure 1 cup "cooked" pasta onto our plates OR so many into a casserole based on how many I intend to serve with it.
If I am making a casserole for 2 persons -- I use 2 cups "cooked" pasta in each casserole; if making for 4 persons, I use 4 cups in the casserole and so forth. For things like chili, stew, or soup -- I measure the total serving for each person, say 1 cup servings but Fitday could help you be even more precise.
... hope this helps you a bit.