The first time (and several times after at WDW)) I had a Monte Cristo sandwich was at Disneyland in 1973. It was dusted with powdered sugar and served with too-sweet raspberry compote. Since then, I've tried Monte Cristos in other restaurants: Some are dusted with powdered sugar, some aren't. Raspberry compote seems to be the traditional side for dunking, but I prefer blueberry compote that I make frequently. It's good on pork chops or pork tenderloin.
I'm not from the south but never understood the chicken & waffle thing. When we attended a wedding in Raleigh some years ago, we found a charming little cafe near our hotel that was only open for breakfast and lunch. We liked it so much that we went twice. Chicken & waffles was on the menu, and we thought it was odd. Shrimp & grits sounded strange, too, but I had it the second morning and enjoyed it immensely. I also had scrapple that I had never had previously. I'm up for trying new things but chicken & waffles just doesn't sound right to me. JMO