I thought about doing this on my own network (for caching purposes primarily) but I'm concerned about breaking the "end to end" guarantee of TLS.
Essentially, now a separate box on the network has full access to my TLS traffic and if compromised can silently intercept it (and it would be too late by the time I notice).
I control the box doing the decryption, so it is still my system. I can tell Squid which ciphers are appropriate and whether or not I want to validate the chain or accept anything. All of those controls still exist. But yes, I would be concerned as you are if I were using a proprietary proxy like Bluecoat or Websense.
Oh, that’s a neat one and would be very valuable for me. We have poor internet access at home and would be cool to reduce traffic going out to the net.