Questions about controlling and/or logging web access seem to crop up quite frequently, and SQUID always gets mentioned. I use SQUID on Windows at many offices, but it's not the easiest app to configure. Over the years I've come up with a simplified config and I've just put this on http://www.ratsauce.co.uk/notablog/squid27setup.asp
If anyone has the spare time maybe they'd like to take a look and see if this is a useful way to make life easier for the stressed sysadmin.
JR
Thanks to everyone who responded. I'm going to mark this as answered now because it's been lying around long enough.
The point of the original question is that SQUID is hard to configure, and that I think I've come up with an easy way to configure it that I wanted to share. I've had quite a few downloads of my config, and in fact I've answered half a dozen ServerFault questions by pointing them to my link; with generally good results. So it was worth the effort :-)
JR
You may want to look into untangle.com they make a software appliance that includes software that does various web filtering that might be a replacement option for setting up squid. I do not believe their appliance does caching though. They primarily target unix as the target operating system but they do have one for Windows (http://www.untangle.com/Re-router-Technology) that you may want to consider.
Here are a couple of the links that I used when first getting into Squid. We run it on many Windows machines.
I remember one of the hardest challenges (for me anyway) was installing Squid as a service and then hiding the output. I will continue to look through my notes, but here are a few of the my Squid bookmarks:
This one has some commnad line switches:link and this one is more of a guide guide
I will update this answer with better info when I get to my office this morning and can look at my notes.
EDIT: The command that I am referring to that will run Squid as a service (at startup) and hide the output/command window is squid -i -n squid -O "-D"
Also, in my setup, the Squid folder lives in the root of the C drive. For configuring the .conf file I referred to a bunch of different Linux sites.
ANOTHER EDIT: Because I am an idiot, I actually just now read your entire post and have downloaded the .zip. My apologies for not posting any useful information and thank you for the zip (which I will comment on once examine it).
I suggest you take a look at Cygwin, as it contains many services; such as Squid and may offer an approach to installing it that is easier than your previous methods.
Squid on windows is good. In fact I'd used and ran it for more than 1 year, one of many Internet Café's I served. Try: http://squid.acmeconsulting.it/SquidNT27.html
There are instructions to follow, to fully run your Squid Proxy in Windows. And if you want to add a Squid Monitoring/Management you can Install cachemgr.cgi, which is optional.
Or Try http://www.krakenreports.com/index.php?subPage=krakenConfig also free but Donations Required.