i just want to comment on the mechanical side for a sec, since most of the posts here on the narrative, I agree with. If you pick up a holding and wealth, that is essentially automatic barter with strings. It is always worth it. You can still do your gigs outlined by your playbook to get more barter (note: the hard holder and MaestroD with automatic-wealth lack these). And on top of that at the start of every session you might get more from this holding, maybe that completely covers your barter for the session and your gigs are pure profit rather then half spent on staying alive. But as all things that give you stuff in the apocalypse world, it gives your trouble and story too. (Which in my opinion is actually more interesting then the barter)
So you roll a 10+ and you get all the goodies from your wealth and your gigs. That's like what, 2-5 barter in total? Damn. Best find stuff to spend it on!
So you roll a 7-9, you get whatever barter you set the holding up with, maybe immediately spend that on your session's living expenses. You worked your gigs too so you've got 3-barter there-abouts more now in your pocket. And your holding even gives you another narrative prompt, a problem to solve, a apocalyptic event from which to spring board or ignore and watch fester like an open wound. Sounds pretty awesome to me.
So you roll a Miss, your gigs now go to living with only a little left over. Maybe everything's going to shit. The holding is certainly not in a good way and needs to be helped now if it's going to survive. Your character's narrative attachment to this holding is now being tested, does it survive? do you? Seems to me like this provides so many awesome opportunities that even if you missed the roll EVERY SINGLE SESSION, it would just mean your life is really not boreing. This is the apocalypse world, it's suppose to be like this.
Sounds to me like the holding gives your story, narrative, sometimes covers your living expenses, sometimes it does more then that, sometimes it instead gives you immediate pressing goals. Super cool.