1) An attacker getting access will only be slowed down/detected if your firewall filters outgoing traffic, which practically no one does because of the inconvenience and maintenance costs. You also need to lock down outgoing traffic to port 80/443, which is how many intrusions download their payloads and calls home for instruction. If you however accept the cost and do use a outgoing filter, it's quite effecting in detecting and stopping attacks, and it is something I recommend for defending assets with high security demands or high risk.

2) As for configuration errors, it depends on what kind of practices you use as a sysadmin. Do you download and run random scripts found on blogs, use experimental versions, and do not spend time reading manuals? Or are you someone who will only run a Debian stable, has verbose settings in aptitude and reads patch notes? It's been a long time (i.e., almost 20 years) since the last time I saw a program that allowed vulnerable interfaces to be accessible on the network without significant warnings in the manual, comments in the config file and readme. Projects and package maintainers have significantly stepped up their security practices, that by the time something reaches stable it should be matured enough that shooting yourself by accident is difficult.