Most of the frustration comes from dealing with the phone calls, waiting on hold,
This is not something they do over the phone. You have to show up, in person, with original documents in hand,
It doesn't require Bob's "brain work",
But it does require a vehicle, especially in suburban and rural areas, because you have to travel, in person, to the jail / prison / hospital to get the paperwork, and then take that paperwork, in person again, to the SSA office. And there are even more steps if you're on public health insurance etc.
just that Chris manage to find it in himself to deal with the annoyance.
There's no way Chris could manage it on his own, even if he was willing to do the legwork.
the sprawly outer areas built in the 1950s-1980s not so much
They didn't stop in the 80s.
God if I knew being retarded on the internet my whole life would be arguably easier than an actual career path I'd be right up there with Chris.
Easier, maybe, but far less successful. It's not the sort of life that can provide things like stability, financial security, …dignity.
The money goes directly to them and into their accounts.
Then why did Barb have to demand a sizeable portion of it every month from Chris? Had it gone directly into her account, we would have heard Chris complaining about that, not complaining about handing over money to Barb like he did.
Chris has his own account into which his tugboat is paid. We know he has access to Barb's accounts because he has transferred money between his and hers. We don't know if Barb has access to Chris' account. I suspect she does, but was lazy enough to let Chris deal with it.
or will they be varmints like coyotes and squirrels
Feral hogs.