@aGeekHere:
For https you can use wpad.
Sites that have popup loops are normally bad sites which can be blocked by squidguard and a block list.
You can also enforce google safe search for all clients.
Not that simple, although this is the beginning of the right approach.
Explicit (meaning not transparent) proxy is mandatory otherwise HTTPS goes direct.
(one could intercept even HTTPS in addition to SSL-Bump… this is another approach but not that simple)
WPAD will, basic, get rid of the burden of manually configuring each and every device so this it relies on proxy. No more (not less)
Then, second step, proxy.pac content will tell browser when to use proxy (and which ones) or not.
Next step is proxy configuration:
blacklists at Squidguard level will prevent to access unwanted domains (including proxies, redirectors... :P) and direct IP ;D ;D
page content can
not obviously be controlled for HTTPS flow (unless you enable SSL-bump, AKA MITM)
ad-removal is partially done with blacklist too