Do you have a link for the DTLS support in OpenSSL? I have not been able to find much on that when googling :/
That's why I called DTLS a "can of worms". OpenSSL has supported it since about 2005, but there's no real documentation or examples. Your best bet would probably be to read the DTS specification, assuming you already have a background in regular TLS...
Using SSL for communicating with the server seems like a large amount of overhead once the client is authenticated... Is there a performance overhead by sending every packet through SSL?
Most of the overhead is involved in establishing the connection. Overhead once the connection is established is pretty minimal - enough so that it's unlikely to be a bottleneck in this day and age.
When the client is authenticated, as long as I map the PlayerId from my database with the IP that the user is authenticated with, can I send any non-sensitive data (like location updates and chat messages) over as plain text to the authenticated IP?
I assume you mean the IP + port #, since IP alone isn't sufficient to identify a client behind a NAT gateway. And yes, if you aren't worried about wire tampering, that's a fine way to go. But the initial authentication every time they connect needs to be secure.