The general way to send emails on Subversion commits is to use the hook script provided by Subversion. Details of running that script on Windows are here:
https://ctf.open.collab.net/sf/wiki/do/viewPage/projects.svnedge/wiki/CommitMailerOnWin32
It sounds like you have this working successfully, but just making sure this is the hook you are using.
I am not aware of this hook not supporting SSL. It uses Python to send the message so would likely just be based on what Python mail module supports. It seems like it would support this. I suppose there are other hook scripts out there, I know there is one in Perl.