To get really fancy:
For a while I had 443 and 22 forwarded to sslh in a jail. sslh split SSH traffic to FreeNAS and SSL to stunnel in a jail. stunnel decrypted the stream and directed the traffic to another sslh instance. sslh would then send HTTP traffic to an nginx reverse proxy (several web GUIs, directory listings, etc.) and SSH traffic to FreeNAS. Oh, that first sslh instance also accepted port 80 and forwarded the traffic to nginx, but all that would be served back was a redirect to SSL.
This took quite a bit of diagramming to keep straight as I configured things.
While very impressed with myself that such a contrived tangle actually worked, I replaced all of that with OpenVPN running on my router. The nginx reverse proxy is all that remains and that's just to make the web GUI URLs easier to remember.
If I start running in to many networks that block OpenVPN I turn the tangle back on, but it hasn't been an issue so far. I've also been meaning to look in to proxying over DNS, but that's certainly not high on the list either.