Answer to 1):
With current technology and best practices, there really should not be an absolute failed backup or lack of notification. I would go so far as to say the IT guy is simply irresponsible. Using NAS appliances and including redundant Internet backup methods, such as Mozy, should provide sufficient backup with minimal failure, unless there is a physical issue or extreme power outage. There should also be some type of automated monitoring tool in place, such as Level Platforms, which provides 24/7 coverage and notification of exceptions. These are the current best practices. None of the above are overly expensive, especially when comparing the cost to loss of critical business data.