Since you want some food production, you might consider making the shade tree dual purpose. Standard sized apple trees are nice shade trees. They might produce more than you want to deal with though. Pecans are very attractive trees and the webworms aren't usually a problem.
Standard trees are a lot hardier than the full dwarfs. Some of my full dwarf apples and all of my dwarf pears died about the time they were mature. Springs are very wet and summers are often very dry in this part of the state. We get a lot of wind too. The pears mostly died of fireblight. The apples fireblight and drought. I actually had one mature dwarf apple die with a full crop of almost mature apples on it. It didn't drop the apples or even the leaves. They looked like they'd been dehydrated. I'm replacing them with a standard sized pear, a couple semi standard apples, a white mulberry, and two Nikkita's
Gift persimmon. I'm going for variety now so a single disease isn't likely to affect every tree. I also have sea berries, autumn olives, and goji berries.
I'm not familiar with hybrid linden. I've heard some hybrids have very invasive
roots and weak branches from the fast growth. Honeybees like linden though.
There seem to be quite a few people from MO on here. Always nice to hear from another Missourian though.I haven't been to Bowling Green. Is this
thread about your own yard? I think St Louis has less droughts than we do.