Driving from SF to LA is *hell* on holidays or in bad weather, but it's short enough that high-speed rail will get you there about as fast as flying (considering the extra check-in and security burden at the airport)
General mass management tends to be done via a distributed ssh shell wrapper. There's not much mass management that needs to be done, usually, other than "update your PHP source/config files and restart the web/proxy/whatever server" or "go install updated packages".
The fun comes when individual servers are borked in some way and you have to beat them back into shape.
We're looking into puppet, but haven't deployed it yet.
With your bare hands?!?