Rock chestnut, scarlet and black oaks. And most pines require little soil/nutrients.

Good suggestions to think about. S

Scarlet Oak would be out as it performs poorly in alkaline soils.
Some sources say the same about black oaks as well, including a local grower.

Any alkaline tolerant pines that can be exposed to winter winds?

Hickory...Bitternut, Pignut, or Shagbark.

As for Pines...are-there-any-pine-trees-that-dont-mind-alkaline-soil-zone-5

Too bad my own recommendations from that post are too slow growing!

Hickory would be excellent but I don't know how I'd ever get one going in this exposed area. You need to have those in the shade to get rolling and by that time they have a taproot. One to still watch for....I'd like to have a Bitternut and Shagbark.

What happens if you cut the taproot?

How "alkaline" is your soil? Limestone areas in the nearby Cumberland Valley can be quite alkaline on/near a limestone outcrop, but fairly acidic close by out of the outcrop area.

Bitternut hickory tolerates alkaline soil well. Also hackberry, catalpa & black walnut. So does stuff in the pea family -- honey and black locust, redbud, coffee tree, yellowwood. And obviously VA juniper, aka red cedar.

Generally its between 7 and 8 around here.

I have two samples ready to go for testing!

I might have to just use several Coffee Trees. Would go yellowwood too but it grows very slowly around here for some reason.

With regards to your earlier question on trimmed taproots for hickory. Not ideal, but they will survive. I planted a shellbark hickory whose taproot was pruned ~12" below the root flare - the root was as thick as my thumb at that length and just lopped off. I made sure to water it regularly the first year, occasionally the second, and it has been growing well.