You have a lot going on…maybe too much for just starting!
Feel free to look thru my other posts that document my ongoing "journey".... :-[. Its a learning curve to say the least!
Some thoughts:
Careful with "...mostly working the way I want..."....its what I don't know that scares me the most!
Regarding logging: Not all pfBlocker rules showed up in my firewall rules, I look in my pfBlocker "Alert" tab AND in my firewall log. I tried squid but never had much luck...kept breaking things. I use the Snort package and pfBlocker instead. Maybe 1 day I'll be able to incorporate squid but it shut me down as well.
Learn how to create fixed IPs for your clients, learn how to create aliases, specifically port alias and devices aliases(with fixed IPs)...knowing this, you can make some tight rules. Its pretty easy...I was advised early to get my rules right as they are the critical element in a firewall.
Get your rules down first...the default "Any rules" that come preset, IMHO, are pretty liberal...I wanted a tighter setup and restricted the ports and devices. I set up aliases for ports I want to allow access to and devices I want to allow.
When you want to deinstall a package, make sure you do so correctly, some have "Save settings" which makes some of the features and rules "linger" even after you uninstall the package. Install squid again and look for this "check box" click save, reload or update(Cron event for pfBlocker...not sure if squid has this) and then uninstall again.
As mentioned I replaced my default "Allow Any" rules with the specific ports I wanted to allow access to, the most common being 53(DNS), 80(http) and 443(https), however I later discovered by looking at my firewall and missing google voice calls that other ports were needed for my Google voice. I suspect Crashplan has some specific ports needed as well(I don't trust any cloud services by the way but thats a seperate post!).
I too am looking for a good "dashboard", some one recomended "Security Onion" as a good solution but it is not a pfSense package, I believe it requires exporting your data to another program. Never done it...apparently this is a gap with opensource software. If you find a good package let me know...how is ntopng working for you?
Learn how to do an "Easy rule" from your firewall log, it adds a rule that will allow you to pass or block an alert. Keep in mind, in my experience you need to go back to the interface, that the rule is added too and move it up the priority list(remember pfSense looks at rules in the order they are placed on the interface i.e. top then moves down). The easy rule also allows you to go back and modify.
I suspect if you do #5 above and uninstall squid correctly you will be functional again.
Consider Snort in monitoring/"IDS" mode to start, after you monitor the alerts you are getting(similar alert tab as you find with pfBlockerNG), switch to "IPS" i.e. kill nasty connections.
pfBlocker has some cool filtering functionality but a little tricky to get fully going(sounds like you enabled geo blocking only)...learn how to set up DNSBL and IPv4 lists in pfBlocker.
Hope this helps... Just my 2 cents, open to feedback, alternatives and rude remarks from the community if my suggestion is wrong!