I'd love to see the old street poles removed with the new lighting. Otherwise looks great. I'm hopeful dead trees get replaced soon - the Quad's trees and buses are kept quite lovely.
100% the old street lights have to go!!!
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As to the trees...........for the non-oaks, (elms and/or honey-locust) they can be replaced this fall; I would say November ideally, but later this month isn't terrible.
Though they really should either get slightly smaller ones, or they shouldn't trim the roots so much.
When trees are transplanted the roots are invariably trimmed, pretty much unavoidable. But over-trimming really stresses the tree.
Imagine being a 6ft tall human, and suddenly having your digestive tract shrunk to the size of a 6 year old child.
Your body is just as big and requires just as much energy, but the mechanism for gathering that energy is severely constrained.
That's one of the key reasons to move trees when they are in their dormant phase.
They require far less energy and water, and they have time to re-grow their roots gradually.
But an 80% cut back can be pretty lethal regardless.
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Oaks should wait til spring if they need replacing.
Nut and cone-bearing species both do much better planted in spring vs fall.