A local proxy that does analysis or filtering such as privoxy or a proxy that connects to remote computers and increases tunnel length?
You want to replace Tor with another proxy software?
Well, if you want to use a proxy similar to Tor which connects to remote servers such as JonDonym then I don’t see how your other ideas would relief connection interrupting or slow connection issues?
In theory it may be possible (depends on proxy software) but undocumented / unsupported.
Indeed. At this time it’s unlikely that I would work on something like a Proxy-Gateway VM that can be chained with Whonix-Gateway unless paid.
In principle, in theory this is possible:
Whonix-Workstation ™→Whonix-Gateway ™→Proxy-GatewayUser→Tor→Proxy→Internet
Also this is possible:
Whonix-Workstation ™→Proxy-GatewayUser→Proxy→Internet
My notes on that subject might be outdated:
Dev/Inspiration - Whonix
Because of attack surface and potential leaks.
Anonymize Other Operating Systems a similar topic but related:
Whonix ™ maintainers have not researched yet, if there is any feature in DHCP servers that would be problematic in the use case of anonymity distributions that use a two machine isolation approach. (Help welcome!) [archive] Maybe there is such a feature, maybe not. If it exists, maybe it could be easily disabled, maybe not. What is the attack surface here: once an attacker has compromised Whonix-Workstation ™, an attempt to exploit the DHCP server on Whonix-Gateway ™ could be tried. Worse, maybe DHCP has a feature such as “please tell me the IP address of your upstream router”, and that would be your real external IP address and DHCP would answer. To find out if this is actually the case, one would have to read the whole DHCP protocol [archive]. Forum discussion [archive]. If you are interested anyway, please click on expand on the right side.
Better to use static networking without DHCP.