We study bifurcation measurement of a multi-level superconducting qubit using a nonlinear resonator biased in the straddling regime, where the resonator frequency sits between two qubit transition frequencies. We find that high-fidelity bifurcation measurements are possible because of the enhanced qubit-state-dependent pull of the resonator frequency, the behavior of qubit-induced nonlinearities and the reduced Purcell decay rate of the qubit that can be realized in this regime. Numerical simulations find up to a threefold improvement in qubit readout fidelity when operating in, rather than outside of, the straddling regime. High-fidelity measurements can be obtained at much smaller qubit-resonator couplings than current typical experimental realizations, reducing spectral crowding and potentially simplifying the implementation of multi-qubit devices.