For chestnuts, if your place is far north, need to look in cold hardy selections.
I have some hybrid chestnuts that have dieback during any very cold winters.
Another problem is the trees getting too much sun in the winter and getting sunscald, south side of the bark is easily killed when trunk is exposed, good to leave low branches on as I have learned. So they are a little touchier than other trees like apple.
As said above, add some pear trees. do you have mulberry trees on your place, seems like everything is attracted to them during summer season. Add some hazelnuts too, various oaks, and why not pecans too.