First, let me thank you for that interesting and intriguing idea. Tried it in a VM and came across some problems, so i thought i'd share the solutions and improvements with the rest of you. I'm sorry for any grammar-related fuck-ups, as i'm a non-native english speaker.

Software used: Arch i686 2.6.29-3, Tor v0.2.0.34 r18423, Privoxy 3.0.12, Squid 2.7 STABLE6

I only used Squid-IN as caching proxy collecting from the 8 Privoxy instances. Next step will be inlcuding havp into the chain.

1. Tor config

- The "Group" option is deprecated an no longer needed.
- What exactly is the ControlPort for? I didn't see it used anywhere, just Tor throwing a warning about the ControlPort used without authorization. I simply deleted the line, everything still works fine.
- Once everything runs smoothly, logging isn't really needed any longer, is it? Same goes for the other log files.

2. Privoxy config

- The "standard.action" is now called "match-all.action". Privoxy won't start with "standard.action"

3. Privoxy startup script

- The "$PRIVOXY_ARGS" when starting the Privoxy instances needs to be removed. Privoxy won't start, but without them they work as expected.
- For testing purposes and as i'm only using one squid, i deleted the havp and squid lines and used the existing /etc/rc.d/squid, so every chain link can be started/stopped seperately.

4. Squid config

I had a problem getting your config up and running, haven't found out exactly where it hangs. I edited the squid.conf.default to mainly do the same.

- "cache_peer localhost2 parent 8129 0 round-robin no-query" won't work, as squid understandably can't resolve "localhost2".

Instead use:

"cache_peer localhost parent 8129 0 round-robin no-query name=localhost2" and corresponding, which will work just fine.

Problem with the first line: it works, but only the first entry (which correctly reads "localhost" as host), so it doesn't really improve anonymity with only one Tor-session effectively used.

Using this config i got the whole chain up and running quite stable. Btw, i'm using encryption for the VM-disk, one never knows when it may come in handy. Hope this helps someone who tried it and ran into the same problems.