Yes this is possible with dd-wrt on Netgear.
There is no need of Raspberry (unless you meant to run the remote VPN server on it).
Configure and run VPN server on dd-wrt - and try connectivity by connecting clients. Both tun/tap should work in general (with VPN client running). I tested with tun.
Configure and run VPN client on dd-wrt and try connecting to your VPN server. By default, the router should start directing all traffic (for its own LAN clients) via the VPN server.
So far so good.
The problem comes when you want dd-wrt's VPN clients (and not just LAN clients) to take the same route. With a VPN client running on dd-wrt, dd-wrt's own VPN clients will not be able to connect to the VPN server running on dd-wrt as such. To make it work, see below.
- This is only possible via PBR - i.e. you run VPN client on dd-wrt, but take the router itself off this client, and route only specific clients through this VPN client running on dd-wrt.
With some tweaks using subnet masks, it is possible to include all your LAN and VPN IPs in the PBR policy so that everything (except the router itself) routes through the remote VPN server.
The key is to include dd-wrt's VPN clients' virtual IPs in the PBR. While configuring VPN server on dd-wrt, there is a field for specifying the clients' network and netmask.
If you use this network IP and netmask in client process's PBR policy, your (dd-wrt's) VPN clients will be able to connect to the VPN server running on dd-wrt, and will in turn be routed through the remote VPN server to which dd-wrt is connected as a client.