Amazing what a little "light" reading can do for you, that and stepping away from it all when your eyes feel like they have sand in them.
Opted to restore my pfsense install from a period before I started trying to hide my traffic.
Worked great. Then I followed a more recent DIY to install openvpn and PIA, and what do you know, it freaking worked. I even went to a bunch of dns leak test sites, and voila, NO MORE DNS LEAKS!
My traffic is protected from prying eyes, and my children can't see things that they won't forget by using pfblockerng
However, this leaves me without the ability to remote into my pfsense box from work. Another project for another day!