Question 2: For operator's gigs, some of the gigs seem kind of ambiguous to me. For example what would Enforcement and Campanionship include? I see enforcement like racketeering and companionship as being a mooch off of someone with barter to spare and wants someone pretty to hang off their arm. But do you see these as having more applications? I'd like to spice them up a little in my games if possible.
Generally, I see gigs as doing something for/with someone else, or between other parties; they're jobs that, usually, someone is paying you to do.
So, "enforcement" could be going around to various satellite communities and making sure they're paying their tribute to the local warlord, or acting as an inquisitor for a cult leader ensuring the "purity" of their followers, or being the eyes-and-ears off a gang leader making sure the rest of the gang are "following the rules"... heck, the Operator and their crew might be local "law enforcement"...
And companionship could be the literate Operation reading Golden Age stories to the scary, blind Hardholder once a week, or acting as a nursing crew for a local healer, or riding along with the caravans making sure the drovers don't get to squirrelly out in the wastelands... and, certainly, it can be "arm candy" as well... an Operator with a crew of "lookers" whose presence livens up any gathering.
Lots of possibilities!