GPO, OU and best practice and advice

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Presently I have my OU setup per work areas:
Managers
Accountants
Sales
Tech

Some of the techs and sales people are remote (laptops), some are local
(desktops), and some members of each OU need to have Web Filtering turned on.
I can set the GPO for webfiltering to set the proxy ID, but can't get it to
stick unless I put the user in an OU called WebFiltering and out of thier
business unit OU. Do I need to setup OUs under Management per:
Management
Office
Web filter
Unfiltered
Remote
Web Filter
Unfiltered
to make this work?

Any thoughts on when a local (in office) laptop user goes mobile? He won't
be connected to our network to access the proxy unless he starts the VPN
(Cisco) first.

I'd be interested in hearing how others have solved this issue.

I tried just using security groups, but it wouldn't enforce the web filter
policy.

Thanks in advance for the advice.
.

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