Hello Bryce,
Regarding question number 2
2-The ASA and the Cache Engine(Iron port)keeps the communication by sending keeps alives but this ones are really week( I am here, I see you)
now regarding why the webfilter process stopped I am not sure, I know there are some logging messages related to WCCP events as for example:
332001: Unable to open cache discovery socket, WCCP V2 closing down.
But It would be a better way to troubleshoot the Iron port itself.
Regards,
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Julio
Julio Carvajal
Senior Network Security and Core Specialist
CCIE #42930, 2xCCNP, JNCIP-SEC