It just doesn't seem very realistic for a person to keep a business going if she needs to be working elsewhere to remedy the loses the damn thing imposes on her.
The
business isn't imposing any losses. The business itself (by itself) is barter neutral. Yes, you might be able to charge a fair amount for booze or sex or drugs or whatever, but you have to have gotten that stuff from
somewhere. Getting all that stuff has a cost (and a hook - who are your suppliers?). Housing all of that stuff has a cost (and a hook - who is your landlord and what do you owe them?). And most importantly,
protecting all that stuff has a cost (and a hook - do you have your own muscle on the payroll, or it someone else offering protection in exchange for a cut?). So yes, you provide a service, but that service has costs of its own. In total, if you don't do anything special (or stupid), your profits and those costs offset.
And yeah, if you chose to live in your establishment, I might also knock off the 1-barter a month living expenses. But maybe not, depending on what it provides. A roof over your head is great, but a man can't live on sex, booze, and drugs alone (despite what Keith Richards would have you believe). Sooner or later you gotta eat.
Absent having
connections (which is essentially what
fingers in every pie represents), if you want to be rolling in barter you've gotta do what everyone else has to do - hustle. But it doesn't have to be outside your establishment. A good business owner is going to leverage his establishment to help him hustle. Want to make more money off the drugs? Invite your source to dinner, then poison the fuck out of him and tell him that the only way he gets the antidote is by telling you where he gets the stuff. Spoiler alert - there's no antidote.
Expand into a new and lucrative side-business (a perfect use for
moonlighting). Welch on a deal. Overcharge a desperate customer.
Just remember that no matter what services or goods you're offering,
honest businessmen pretty much never get ahead in Apocalypse World.