I don't use SSL on the Premise site since it's never been opened up to the outside. But I do have Static IPs as I have Comcast Business and some servers behind my router. So I could theoretically setup anything I needed to. I have an internal domain setup via my email server, but my Premise/Sage box is a standard Windows 7 setup. I've been wanting to build a new 2012R2 box, but just either haven't had the time or the money. Always one or the other
But I'd be glad to play with it. There is a free SSL certificate organization that is a trusted authority. StartSSL. At least their standard level is free. They have EV level certs for purchase for eCommerce sites.