From my experience in southeast NE(heavy clay on my farm), I would recommend pears only. My chestnuts have been in the ground for 7 years and are only 10' tall at the most. (I did start them from seed) I planted several pear varieties(all whip size) since then and they are already producing, (3-4 years in ground which would probably equate to how old the chestnuts are). My pear trees that are 10 to 14 years old have been producing great crops (almost yearly for every tree). The deer hammer them and my family loves them as well. There is plenty to go around. I don't baby my pears but I do prune every 2 ir 3 years.
I planted them, made sure they had adequate water the first year and then they have been on their own. I did the same with my chestnuts. I'm sure they will someday produce but I'm 56 and don't know if I'll see it. If I'm blessed to a long life then Im sure I will but one never knows. The pears will still be viable if I am blessed with that long life and for the next tenants.
Kieffer and the offshoots of it are great deer pears and good for canning/baking. Asian pears are incredible eating pears, salad pears, canning, dehydrated, and baking. I have pears that drop from August into December.