[Edit: I answered the first half of my issue, so I'll edit this to address the second half.]
/etc/monit/monitrc looks like this:
set mailserver
smtp.server.net
port 587
username "USERNAME"
password "PASSWORD"
using tlsv1 with timeout 30 seconds
using hostname "server.fqdn.com",
smtp.server2.net
port 587
username "USERNAME"
password "PASSWORD"
using tlsv1 with timeout 30 seconds
using hostname "server.fqdn.com"
sudo service monit syntax
spits out this:
/etc/monit/monitrc:57: Error: syntax error 'smtp.server2.com'
At first I had the wrong using/with syntax like this:
using tlsv1
using hostname "server.fqdn.com"
with timeout 30 seconds