I understand you your speaking quite well as I have a few family members by marriage of German decent. I have spent a great deal of time with and have come to be able to pickup what they are saying quite easily. As far as the reading you mentioned goes, reading is not the issue. The issue is understanding the terminology and most writings about pfsense, don't go into great detail " in laymen's terms " on what things do in the program. When coming to these threads, one really has to rely on the quality of the responses which can be shaky at times. Answers are answers; but if they are not intelligible by the reader, then they haven't provided the help desired and this is my biggest issue so far. I really appreciate that you have taken time to assist and it has definitely pushed me to tinker a little harder and see what does what.
For squid and squid guard. since I figured out that the blacklist requires daily updating, I followed the instructions I mentioned for cron and it seems to be doing what it is supposed to. Frankly, I'm a little blown away that squid doesn't have a native option for this.
For proxy and wpad. I worked my way through he directions and the proxy works. WPAD not so much. Even though I created the files, placed them in the correct directories and added the DHCP rule, my computers still bypass the proxy unless I go into the internet option on my browsers and point them to the proxy. I can verify this using light squid. Additionally, with squid guard, the rules set for website types don't pickup unless, I add the setting for the proxy in the browser.
These above are the issues that still remain and I'm not ruling out user error in my settings. Just really hoping that someone else has experience the same issues and can pass along what they did to fix them.