Yes, they have refillable mugs. I own at SSR so it's what I'm most familiar with... when I was last there in January the mugs were labeled "Disney Vacation Club" so I think the answer is yes, you would have to buy them twice.
I would definitely split my stay be ENDING with whichever DVC resort you select. There isn't a Disney resort I don't absolutely love for one resaon or another but be forewarned that after you go DVC it will really spoil you!! With a family of 5, it won't come as a surprise to you how much easier life is with a washer/dryer.
The kitchen also comes in quite handy even if you aren't cooking large meals.
DD (21) and I staying at AKV for the first time in May... can't wait!!!
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