I just read through your PTR. I'm sorry your sister will not be able to join you, but you all will still have a great vacation. We stayed at Pop last year and loved the food court, the Tie-Dye cheesecake is now my favorite Disney snack. I have always wanted to go in December to see the Christmas decorations, I can't wait to follow your plans and read all about it.
We drive down for our trips too, we have a 12 hour drive. The drive down usually isn't too bad. We try to just make the road trip as part of the vacation.
PS We were in IN not too long ago for the Notre Dame spring game. I loved Indiana!
We loved Pop Century when we stayed there on our last trip, the only reason we weren't going back there is because we like bigger beds, so when we needed two beds it made sense to stay in a value. I didn't get to try the Tie Dye cheesecake last trip because our only time we ate at the resort was the first and last days of our trip and I forgot the first day and the last day I was starting to get sick and barely ate anything. I'm hoping to try it this year.
We drove down from Albany(which is about an 18 hour drive) on our second trip and it wasn't too bad. DH doesn't mind the drive and since it's a lot cheaper than flying it's a way to cut costs when we have the ability to add a couple days on each end of the trip. I'm looking forward to being able to go to the Disney outlet to get our souvenirs, I love the stuff that Disney sells, but I do not love the prices in the parks. It also allows us to be flexible on our departure day so we get more Disney time.
I'm glad you liked Indiana, I've lived here all my life except for the two years DH and I spent in Albany and I'm definitely happy to be back home now. New York was definitely not for me.