In the real world of female prostitutes
Pimps hold on to their girls by emotional support, and if that doesn't work it's drugs, intimidation adn outright force.
Ray obviously like Tanya, at least as a working partner. But just, exactly, why should Ray, or Jason, be afraid to tell Lenore to go eff herself? We have never seen that she has any muscle backing her up.
Lenoer is more like an annoying insect that everyone, except, perhaps, Tanya is afraid to swat. In real life, and I know this is nowhere near "real life" Ray or Jason would put a ski mask on and drag Lenore out behind the wellness center and bet her to a pulp as a way of warning her to stay away.