Rhombohedral multilayer graphene hosts a distinctive low-energy electronic structure in which strong Coulomb interactions and nontrivial quantum geometry intertwine to generate exotic quantum states. Recent experiments reported signatures of chiral superconductivity in electron-doped rhombohedral multilayer graphene within the spin- and valley-polarized regime. Here we map the normal-state fermiology surrounding chiral superconductivity in rhombohedral pentalayer graphene. Quantum oscillation measurements reveal an electrically controlled Lifshitz transition between a simply-connected circular quarter-metal Fermi surface and an annular quarter-metal Fermi surface. The Lifshitz boundary itself shifts with perpendicular magnetic field, consistent with the strongly momentum-dependent orbital magnetic moment of the low-energy band. Approaching the transition from either side, the electron effective mass becomes strongly enhanced, implying the formation of a nearly dispersionless band bottom and a strongly reduced kinetic-energy scale. This singular electronic structure produces a regime of exceptionally strong instability in which chiral superconductivity competes with Wigner crystalline phases and reentrant quantum Hall states. In particular, two superconducting regions with signatures of orbital time-reversal-symmetry breaking lie on opposite sides of the Lifshitz boundary and have comparable transition temperatures, yet the annular-side state is suppressed by a substantially smaller perpendicular magnetic field. Our calculation finds comparable chiral pairing tendencies on the two parent Fermi surfaces while producing a much lower orbital-Zeeman pair-breaking scale and an additional finite-momentum pairing tendency for the annular state. These results identify Fermi-surface topology as a key control parameter for chiral superconductivity in rhombohedral graphene.