I really enjoy counting calories as a method for weight loss, mostly because I can still eat the things I like (just not the portions I used to eat). It sounds like it will be a good choice for you, as well, since you'll be using a meal plan for a lot of your food.
If you have access to a dietician, you may want to look into seeing them for an evaluation and diet plan (some schools offer one on campus). I didn't have access to one, so I did what I could do, and that's check online. I Google'd "how many calories should I be eating?" and looked for calorie calculators (I think I used
this one). This gives you a general estimate, but it shouldn't be considered gospel.
After using that website for my starting point, I downloaded Myfitnesspal on my ipod (there are other calorie counter apps out there, I just chose this one because I have friends that use it too), and started logging what I was eating. Check your school website to see if they have nutrition facts for any of the foods, or see if there is someone you can email for it. Most calorie counting apps do have a database with foods in it, so you can try to use your best judgement...it may not be perfect, but it's better than nothing.
Having a calorie range and logging what you eat is going to be a good starting point for you! After doing this, I went a little bit further and ordered a Fitbit One, which is a pedometer that tracks my movement. As I continue to wear it, I can see the days where I am more sedentary than others, and may adjust my calories (I have mine set at 1200 calories cause I'm a shortie, but on my really sedentary days I find I can go a little lower and still be just as satisfied...if I'm hungry I will eat, but I won't eat just because the app tells me to). I will note that most calorie counting plans say never to go below 1200 calories because there is a valid concern of not getting the proper nutrients, and should only be done with a doctor's recommendation and supervision.
Fruits will have a higher caloric value than non-starchy veggies! Some people don't count fruit or vegetables (similar to weight watchers), but I found I was eating too much fruit and veggies and I wasn't in a deficit, so I started counting those. It was a bummer that a banana is approximately 100 calories, but that 100 calories is just as satisfying as many of those pre-packaged snacks you can find in the stores.
There is a little less than 5 months until 2014, and you want to lose just under 60lbs for that first goal. Is it doable? Sure! For me, personally, I find it to be a bit on the higher end of plausibility (it's taken me just over 3 months to lose 20lbs on mostly dietary changes with a little added exercise), but with hard work and perseverance, you can do it! I would probably break up the goal into smaller increments, though, so that it's more rewarding. There is usually a thread on the support forum every month that has motivation to lose 10lbs from the start of the month to the start of the next month, and that might be a great place to help keep yourself motivated!
Sorry for the long-winded post lol!! Trying to stay distracted
I hope this helps!