Setting up cron

First, make sure cron is even installed. Apparently, it's not default. Look under "Admin".

Then, the prevailing command sequence is

cygrunsrv -I cron -p /usr/sbin/cron -a -D
net start cron

Setting up sshd

Start with

ssh-host-config

Yes to privilege separation, yes to local user sshd, yes to install as a service, and default for how to set CYGWIN= at start.

Then,

net start sshd

If you only want to run the thing on localhost, comment any ListenAddress lines in sshd_config except one saying

ListenAddress 127.0.0.1

Permissions required to do that are something you can figure out.