I'm glad you're here, too!
For me the trick is not to abstain from the yummy food but rather to abstain from eating too much yummy food. As a calorie counter I know I can eat whatever I want, but I have to watch the portions. I can have the challah and kugel - but I have to figure out how much is a reasonable portion for my daily caloric intake. I think this is the only sort of diet for me because I love food, and I don't want a book telling me I can't have something I love.
I keep Scripturally kosher, but not rabbinically kosher. I won't eat any of the unclean foods or cook mammals with dairy products, but I do eat chicken and turkey with dairy. I buy products that are either marked kosher or, when exploring the ingredient list, I do not see a reason other than lack of certification that they would not adhere to the dietary rules.
Still, this eliminates a lot of snack and treat foods. Earlier this week I discovered these wonderful kosher marshmallows in the Passover section of the grocery store. They are rolled in toasted coconut and are a wonderful treat at 32 calories. I tend to eat fruit and/or crackers as a snack, so finding kosher ones isn't a difficult thing for me. I can always do a square of dark chocolate and finding kosher chocolate isn't difficult. Of course, keeping chalav yisrael would make it a bit harder, I am sure.
Right now I am really struggling with finding low-calorie dessert recipes for family dinners. I won't use products with artificial sweeteners (Mom's allergic and I think it's unnatural) and it seems like every recipe I find either uses Splenda or Jell-o, which of course isn't kosher. Any suggestions would be greatly appreciated!