NadineNurse,
I know the Connections info can be somewhat confusing initially. First, decide which type of voucher you want to use (either the Quick & Casual or the Vacation Kingdom) and then look at the appropriate restaurants for the kind of voucher (e.g. counter service for Q&C or sit-down for the VK).
For the Q&C, you will receive an entree and side dish (many entrees come with side dishes like french fries at the counter service restaurants so you would not generally add another side in that case), a drink and a dessert. If the total, including 6% tax, is more than $11 then you would come out ahead using a voucher. If it is less than $11, you should use the voucher elsewhere.
For the VK vouchers, you can order an appetizer, entree, drink (non-alcoholic) and dessert. There are a few items at certain restaurants that may be limited to use with 2 vouchers (Rainforest Cafe has an appetizer and dessert like this) but otherwise you are generally able to select freely from the items on the menu. If the total with 6% tax and 15% tax is greater than $29.50 then you will come out ahead using the voucher. If not, then use the voucher elsewhere.
Don't be afraid to ask your server/cast member what the vouchers can be used for. You may find that some are more generous in what the vouchers can be used for and it doesn't hurt to ask.
We will be at WDW from 1/25 - 2/1 staying at the Villas at the Wilderness Lodge. Our group is me, dh and 2 year old dd. Where is your family staying? We are planning to bring bathing suits since the pools are heated but there is no real way to know yet how the weather will be. I imagine we'll be watching the forecasts as we get closer and bringing a bit of something for every kind of weather just in case!
Hope this info helps - let me know if I can help you further!