When I make pies I let the pie pan dictate the amount used. And since I like a LOT of fruit in the pie, it is usually 6 to 8 cups. Depending on how much fruit I have also will dictate which pie plate I will use. Since it is just my husband & I now, I have several 6 inch pie plates that make the perfect size for 2 people. But if we have a large group I use m deep dish pie plates.
We had a "Queen Anne" cherry tree growing up, my mother made 2 attempts to make cherry jam/preserves and neither time did it come out right, but it was great ice cream topping. My mother made the best cream pies, but when it came to working with cherries, there was just something that always went wrong for her. So she gave up and the trees were removed before I was old enough to try.
It sounds wonderful, I wish you the best, because fresh cherries are the best!