It's never too late to start learning.
Looking at Windows 10 these days, I'd advise everyone to start considering open source alternatives for desktop. But that's another story.
I never tried squid on pfsense, I played with it once on a Linux box, and I had two problems with it:
overcomplicated for my needs
fuzzy documentation
As far as I can see in pfSense forums, most of the issues people have with squid here arise from these two problems, and it also seems to make the whole system less stable, and harder to keep up to date.
Pound is a very easy and straightforward piece of software. It just does what it should and that's it - and that's exactly what I need, nothing more. I really wonder how come nobody made a package for it yet, I even considered once I should make one, but you know, making pfSense packages these days is a real pain in the ass.
As for websites requiring client certificates for strong authentication - look for Apache, and forward them with pound directly. I didn't do things like this yet, so I'm not aware of details, but I guess it shouldn't be too difficult.