I have a similar setup, squid was slow and crashing when it had a long time running, crashing every three to six days. I never found out why it crashed. I looked in the log files and couldn't find anything. It just crashed for no reason. There are some post to the least about it. I decided to restart the system everyday from a cron job at 4am. I know that doesn't sound too stable as I'm running it on a linux box but, it worked. It hasn't crash ever since.

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