Direct proxy, no transparent, client -> privoxy -> squid -> http(s) sites. I trust Squid at the tip a lot more. Forwarding Privoxy to another proxy is easy. Read the Forwarding section of the Privoxy manual. Setup Privoxy how you want. Forward to Squid. Follow: https://wiki.squid-cache.org/Features/DynamicSslCert
You should then have the perfect proxy centipede. For bonus fun use dnsmasq and blacklist domains via DNS too.
Things get much more complex if you want to do things transparently. Now you have to monkey with iptables. The idea is similar though. Start with Privoxy getting all HTTP traffic on a router. Forward to Squid. Have Squids dynamic SSL cert on your client devices.
So is privoxy happy handling HTTPS requests as long as it's fronted by Squid? I guess I'm still not clear on how/why that works. I thought privoxy could only handle HTTP.
You should then have the perfect proxy centipede. For bonus fun use dnsmasq and blacklist domains via DNS too.
Things get much more complex if you want to do things transparently. Now you have to monkey with iptables. The idea is similar though. Start with Privoxy getting all HTTP traffic on a router. Forward to Squid. Have Squids dynamic SSL cert on your client devices.