You can monitor the event logs in Windows to see when a users password is expired and an attempt to log on occurs. You need to look for event ID 535, and if you want to, you can narrow the results by parsing for the username you want to monitor.
I do not know of a way to monitor when the password actually expires. It appears that Windows only creates an event when an attempt to log on occurs, and this functionality in SCSP would fall under a custom detection policy, which monitors logs.
From MS site:
Event ID: 535
Type: Failure Audit
Description: Logon Failure:
Reason: The specified account's password has expired
User Name: %1 Domain: %2
Logon Type: %3 Logon Process: %4
Authentication Package: %5 Workstation Name: %6
As far as a randomly generated password, that functionality does not exist in SCSP, and with an Admin password that could potentially be very dangerous. What would happen if the randomly generated password was not delivered, sent to an expired email account, intercepted in transit, or lost?