I've set up a VPS that handles mail, files, jabber, etc. All these services are available only to the local network that OpenVPN creates. For example all of the services will only listen on the 10.55.66.xx subnet and ignore connections from public IPs.
If the communication between my clients and the server is already encrypted, does it make sense to add another layer on top of that? For example forcing http to https, requiring SSL for jabber, POP3/IMAP, etc.? It seems redundant to me, but I'd like to know if there are any considerations that I'm not aware of.