Hey there,
so for support I found a buddy is great, my sister and I are doing our journey together and we then started a blog we are then accountable to anyone who reads it and knows was we are doing (our friends and families know what we look like in minimal clothing and now we know we HAVE to change). We are both moms, my daughter is 2, my sister has a 5 year old and a 2 year old. She actually just posted a blog about exercising with the kids so she could get her work out in.
My suggestions (these are all things that I have done and I am down 50lbs in less than a year)
1. Water. Drink lots of water. There is a formal take your weight, divide by 2 and that is how many ounces of water you should drink a day. Seems like a lot, but our bodies do not need anything besides water for liquids.
2. Cut out soda, tea, coffee etc. If you HAVE to have something caffeinated limit it to one cup of organic coffee a day. Soda is the worse, have you ever seen that video that shows how many tablespoons of sugar is in one can of soda? It is a waste of calories! I used to drink a 2 liters or more of soda a day (mt dew and dr. pepper are my poison). I have been soda free for 7 months now and it feels great. I no longer crave it, I crave water!
To answer your question about milk, if you need to drink it go for 1% it does not have that much more fat/calories than the fat free but has way more vitamins in it. I took a class through WIC that was all about milk and which one to drink. By the end of the hour class it was clear that 1% is the healthiest choice when it comes to milk.
When I made all my diet changes (I'm Paleo as much as possible) I was SO HUNGRY, without all the fillers and such I felt like I was not eating enough. I definitely eat more food now than I ever have but it is healthier choices, and still less calories. I am 1 day away from completing the PaleoCleanse for the second time (I did it once last year) and it is no gluten, soy, dairy, sugar, preservatives, and no processed foods. It just cleans your body out. It take 28 days to get things like gluten and sugar out of your system. Once they are out, you no longer crave them. Its great, I seriously can be right in front of a chocolate cake and have no desire to eat it.
The one big thing I keep thinking about is my daughter, what she sees me eat and drink, she will want to eat and drink. To her just having water (she has NEVER had juice!) is normal. Milk is a treat and is so sweet to her. Our desserts are fruits (frozen grapes are a favorite). I love that I am not only making healthy choices for me, but teaching her how to make healthy choices of her own. Last night at dinner my sister and I went to a local restaurant that is all organic. I read all the options to my daughter (choices are BIG right now with the 2's) She had options of sandwiches, grilled cheese, chili, quesadilla, and grilled chicken. She asked for the grilled chicken. I made SURE she wanted it "Are you sure you don't want a grilled cheese?", nope she wanted the grilled chicken, and for sides she picked broccoli and brown rice. I don't think as a kid I ever would have passed up french fries and a grilled cheese.
Good luck! You can do it. =)