Plan on re-winterizing every time you come back to Indiana from now through the first of March. Last year we went to Florida over Christmas week. I left the camper winterized until we hit Alabama. We took 3 days to drive down and 2 to drive back to Indiana. The first night down we stayed in a motel near the Kentucky-Tennessee border. The second night we stayed at a KOA in Alabama where I de-winterized. We planned this so we'd have full hook-ups and were out of the snow belt. When we got to the State Park in Florida on the 3rd day, we were all set.
Returning home, we completely re-winterized in Florida and about half way. We were back in the snow belt again. We got another motel, and finished the trip home the second day.
I use a combination of "pink" and "blow". My current camper has the black tank built in sprayer. I blow that. So yes, I took my air compressor with us. But the rest of the lines, I do pink RV antifreeze.
We're going to Florida again this year over Christmas and am repeating the same same process.
FYI, a friend of ours has a CLASS-C coach. He travels the various race car circuits. He travels out of Indiana all winter long, and he winterizes every time before returning home.
Remember... you want to re-winterize when your still in the warm climate, not after you've returned to the cold climate.
And, (personally) I prefer to use the pink antifreeze instead of blow only. I want to make sure ALL the water in the lines is 100% removed. Blowing still leaves droplets, and you still need to make absolutely sure your water pump is purged out (no water in it) if you blow only. Just a thought there to consider.