It is very unlikely you could do this and it would probably be a security hole if you could. The OpenVPN server only knows about the remote client and nothing beyond it. It does not even know about the remote LAN subnet.

I guess in theory you could set up a subnet <-> subnet tunnel but that would require routing changes to be made at the far end gateway (not roadwarrior) in order to redirect return packets back to you.

If your roadwarrior is Linux I wonder if it would be possible to DNAT the packets from your server to a single destination on the remote LAN and also SNAT them to the LAN IP of the roarwarrior. Or even reconfigure the tunnel to carry packets to the remote subnet, but they'd need SNAT'ing to the roadwarrior LAN IP as they emerge at the roadwarrior or they will ever come back.

Why are you trying to do this?

I've no idea about encrypted volumes, but have you checked what journalctl (or perhaps "journalctl -xe") says? Also does it get as far as writing any logs - mainly /var/log/boot.log and /var/log/dmesg? Does the command "dmesg" give you anything?

VLAN and site to site VPN for Community or home?

I am looking at switching over from pfsense to ClearOS and had a couple of questions about if I was able to use VLANS and also be able to use IPsec Site to site VPN on the home edition?