Is it possible to do this: OpenVPN client ↔ OpenVPN server ↔ local proxy ↔ internet?

Question

openvpn

You need to create a Wirth. network using OpenVPN which will give users of this network access to the Internet. The key point is that the server itself will "take" access to the Internet through the http/socks proxy. It is also a prerequisite for the server to work via UDP (do not suggest adding a proxy to the client config).

Answer 1

Maybe.

do not offer a proxy to register in the client config

In this case, you must have a transparent proxy. Just redirect traffic from VPN to proxy using firewall. Actually, the interaction of VPN clients with a proxy has nothing to do with VPN - everything is configured in the same way as without VPN.