My two cents:
Do all the proxying and content filtering you want; your child will
get around it. Anyone who is/was young enough to be a kid since the
popularity explosion of the internet will agree with me.
IMO the PC in the child's room (if you INSIST on putting one there)
should either have no internet access or have it on a whitelist-only
basis. IOW, EVERYTHING is denied except for sites you've specifically
whitelisted - nickjr.com, disney, whatever. If he wants to go outside
his whitelist, he can come to the family computer and be supervised.
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