Also, I see that I can order a Dedicated SSL Certificate for $5/month but about using a different hostname, am I right that that means upgrading to Enterprise so that we can swap in a new certificate hostname with a new SSL certificate that would allow second level domains to be covered under *.example.com?
You can on http. On https, they’re going to see a certificate error because the handshake will fail before we can redirect. You could do this either with the $10 certificate (specifying a custom hostname of *.test.example.com) or by uploading your own on either the business or ENT plan. An ENT plan would include a dedicated certificate with customer host names as well in most instances.