The beauty of OpenVPN, is that its an application level solution, so if it helps to visualise it, think of it as you would think of a web server application or a telnet application. In this way, your proposed scenario is perfectly suitable for OpenVPN (and not for other VPN technologies).
This is unlike the IPSec or PPTP VPNs on your ASA (where I think you might be coming from, from reading your comments) which require specific lower level protocols to work (OSI level 3), and which need direct access to the WAN interface and no playing around with NATs and firewall transversals (it IS possible but its not natural for these VPN technologies).