I've been using Squid and Dansguardian for about 10 years (but running Ubuntu server). I would recommend using e2guardian rather than Dansguardian. It is a fork that has added quite a bit and is active (Dansguardian updates and support seem to be fizzling out).
With e2guardian/Dansguardian you can create different filter sets and then direct them to the proper port based on ip range or subnet. In my Ubuntu setup I'm using Shorewall as the firewall and that's how I redirect. I'm working on coming up with the same type of setup in pfSense, but haven't quite gotten there yet.
Here is a link that is specific to setting this up in Ubuntu, but it might give you some good ideas that you can use in your setup on pfSense.
https://www.branchdistrictlibrary.org/professional/ubuntu_precise_dg.php
The info in the link is from a gentlemen who sets this up for a library system he works for, but as I mentioned I've been using a very similar setup at home for many years. The link also uses Dansguardian, but I don't imagine it would be much different setting up e2guardian.
I'm looking at doing something similar to what you're doing with the MAC addresses, but I am hoping to put together a quick web page hosted on my box that will allow my wife to turn access off/on for specific devices (kids Kindles, XBox, etc). In my current setup I have a similar page that will allow my wife to whitelist sites without my help and without her having to login to the administration of the server.
I hope this didn't stray too far from your questions, maybe some of it will be helpful to you.
I'm going to watch this topic in case you post updates on your progress. If you do, maybe I'll post some of mine too since I'm trying to accomplish similar things as I move my environment over to pfSense.