Sammy is a hired hand who gets paid as a kind of subcontractor to bar owner. Bar owner is the one providing services, while Sammy is a worker there.
And yeah, services are a net "drain", or expenditures, on the economics sheet, not a productive behaviour. Same as housing. You people are mixing up "things that make me feel good" with productive behaviour, lol
In your example the bar owner still provide a tangible service, provide the beer wich include storage, fridge for bottle or pump, seatting, a heated room, etc.
Where in the case of Oskar it's never presented what he does as a landlord, you can't even say he provide safety inside the apartement block since male flatmates are planned which in the game setting will lead to women being abused without repercusion.
I think the maintenance aspect of Oskar or safety inside the block should be pushed forward. Even Haven felt more safe, with their visible guards.
My personnal view is that there is a suffisant return to order in the town that the concept of propriety is protected, also given the number of prostitutes there are enough of a prodution of food and/or wealth that people have spare to maintain a high population density of whores.
On a side note I don't like the idea of males flatmates forced upon the player, you pay rent to be safe.