Its really not. You don't need to get everything down to the exact calorie, its a bulk. Go on livestrong.com and it basically has almost every food. Just estimate best you can serving size and you will get an idea of where your calories are, how much you actually are eating, and how much more you need to eat.
What really helped me a lot in school would be to instead of getting water with the meals get the chocolate milk cartons. I forgot exactly how many calories each is, i think its maybe around 150, but i would get 2 with lunch, then another 2 throughout the day. So right there from milk i was getting 600 more calories, plus the protein. Its nothing too fancy, but it really helped me get my calories from the 3000 or so i was eating to the 3300+ needed to gain 1lb per week. I had gotten those figures from livestrong.com
Not sure, look at what worked for you in the past. For me personally i've done pretty well on 5x5 routines or 5/3/1, as well as an upper/lower split. Its all about what works for you. Pick something decent and stick with it for a while