One problem I have with SSH is DPI. Deep Packet Inspection seems to be behind the SSH block in place at a local library I work at. SSH out in any form just isn't possible there, even via a browser-based console (such as that used by Digital Ocean, for example). There doesn't seem to be a suitable solution to get around it offered anywhere. My own fix was to use 3G to do the SSH work via a tethered phone and to use th…
In any case, you can try proxying SSH over SSL using stunnel: http://askubuntu.com/questions/423727/ssh-tunneling-over-ssl
Or you could try setting up OpenVPN, it's easy enough.