With the imminent advent of mesoscopic rotating Bose-Einstein condensates in the lowest Landau level regime, we explore lowest Landau level vortex nucleation. An exact many-body analysis is presented in a weakly elliptical trap for up to 400 particles. Striking non-mean-field features are exposed at filling factors >> 1. For example, near the critical rotation frequency pairs of energy levels approach each other with exponential accuracy. A physical interpretation is provided by requantizing a mean-field theory, where 1/N plays the role of Planck's constant, revealing two vortices cooperatively tunneling between classically degenerate energy minima. The tunnel splitting variation is described in terms of frequency, particle number, and ellipticity.