I think this cycle will be front-loaded with re-applicants. My guess is that applicants will be up for the first half of the cycle but turn down as we move into January. I think Spivey said this will be a flat cycle and I think I probably agree.
It seems like you have a good relationship with this professor so I think it's a great idea to ask him. You could also do the 7sage admissions consulting edit once. I worked with them and it's an amazing service.