Fiber-feedback optical parametric oscillators (OPOs) incorporate intracavity fibers to provide a compact high-energy wavelength-tunable laser platform; however, dispersive effects can limit operation to the sub-picosecond regime. In this research article, we modeled pulse propagation through systems of cascaded fibers, incorporating SMF-28 and ultra-high numerical aperture (UHNA) fibers with complementary second-order dispersion coefficients. We found that the pulse duration upon exiting the fiber system is dominated by uncompensated third-order effects, with UHNA7 presenting the best opportunity to realise a cascaded-fiber-feedback OPO.