Though we never purchase the dining plan, we wing it all the time. I always make our one or two must-do reservations and wing the rest. We even winged a few reservations over Christmas week (was able to get day-of reservations at Chefs de France). If you aren't picky, you'll be fine. I always just look on the phone app about 2 hours before we want to eat and find something close to where we think we'll be in the next two hours. I've gotten some great last minute reservations - Via Napoli, Cape May dinner, Biergarten, Garden Grill, etc. On our next trip, I'll probably just make a reservation at Tiffin's (if it ever opens!) and that's it. It sounds like you have your must-do's already booked. I think you'll be fine.
