Yet again, I have researched a workaround for when ASO breaks something - in this case, SSH and scp.

Here's the end run I came up with to get ssh and scp running from my cygwin setup:

#!/usr/bin/bash

# echo "Trying to scp a file to the laptop..."
# scp -o PreferredAuthentications=password,keyboard-interactive -oHostKeyAlgorithms=+ssh-rsa okbanlon@okbanlon.com:/home/okbanlon/turnip/spock-curious.jpg .

# echo "Trying to scp id_rsa.pub to shiva.pub on okbanlon..."
# scp -o PreferredAuthentications=password,keyboard-interactive -oHostKeyAlgorithms=+ssh-rsa /home/philippe/.ssh/id_rsa.pub okbanlon@okbanlon.com:/home/okbanlon/.ssh/shiva.pub

echo "Trying to ssh into okbanlon.com"
ssh -o PreferredAuthentications=password,keyboard-interactive -oHostKeyAlgorithms=+ssh-rsa -l okbanlon okbanlon.com

I did some screwing around with generating various types of keys on the cygwin laptop setup, so that may be muddying the waters. The big deal here is that I finally bludgeoned the ASO machine into doing an interactive password prompt to get logged in.