An interesting question, and to answer I doid a quickie test run of both vs CF.
Of the 2 I would suggest GlassWire over PortMaster (the latter doesn’t always play nice with CF). With regard to Glasswire, it has a very pretty interface, and if you find value in the non-malware related Network Monitoring thingies it would be fine.
However I was rather surprised that a modified Coinminer had the abilityto connect out the BlackHat Command without showing up in the Netwrok activity screen- but note that I used the free version (with the Paid version all Outbound connections would be handled similarly (but more annoyingly) to CF with the Firewall in Custom Ruleset mode.
Having Portmaster & CIS on your PC at the same time will require a powerful PC configuration, as these 2 programs are demanding in terms of resources.
Personally, I don’t see the functional benefit of having both.
In terms of filter rules, with Portmaster you can do a lot of what CFW does, but I find it less flexible, more cumbersome and less pleasant to use.
Portmaster offers 2 things that I find interesting: it uses filter lists like uBO does and can prohibit direct access to the Internet (programs that want to access the Internet without using the DNS).