I'll answer the easy question first. No Cool Whip is Core. Some are low calorie enough that one serving is no points. I don't count points for my Cool Whip unless I use a lot in a recipe.
Yikes on lunch! I have a hard time and I'm retired. I think salads and fruit with FF cottage cheese would work for you. Consider soup in a thermos. I love Healthy Choice split pea with ham and Progresso Lentil. I make a Cornmeal chicken recipe that I absolutely adore cold. It's on our menu board. Hope this helps.
That's a tough one! I like to cook chicken in the crockpot in ff italian. It is very good cold and would make a good sandwich or topper for salad. Or just by itself! Some homemade core hummus or other dip, veggies, core cheeses, soups....hmmm, I'm repeating everyone else here....I'll think about it!
I make a couscous salad with diced cucumber, tomato, and scallion. I make the couscous with low salt chicken broth, fluff it, add the diced veggies, a splash of olive oil and I use apple cider vinegar. It's yummy cold or room temperature. Hope that helps.
Are you able to take a cooler that has a cold-pack inside to keep things sort of cool? A baked potato with FF cheese and sour cream would keep well, as would bananas and apples, sliced tomatoes, even light string cheese (only 1 point).