We investigate the gravitational lensing properties of lines of sight containing multiple cluster-scale halos, motivated by their ability to lens very high-redshift (z ~ 10) sources into detectability. We control for the total mass along the line of sight, isolating the effects of distributing the mass among multiple halos and of varying the physical properties of the halos. Our results show that multiple-halo lines of sight can increase the magnified source-plane region compared to the single cluster lenses typically targeted for lensing studies, and thus are generally better fields for detecting very high-redshift sources. The configurations that result in optimal lensing cross sections benefit from interactions between the lens potentials of the halos when they overlap somewhat on the sky, creating regions of high magnification in the source plane not present when the halos are considered individually. The effect of these interactions on the lensing cross section can even be comparable to changing the total mass of the lens from 10^15 M_sun to 3x10^15 M_sun. The gain in lensing cross section increases as the mass is split into more halos, provided that the lens potentials are projected close enough to interact with each other. A nonzero projected halo angular separation, equal halo mass ratio, and high projected halo concentration are the best mass configurations, whereas projected halo ellipticity, halo triaxiality, and the relative orientations of the halos are less important. Such high mass, multiple-halo lines of sight exist in the SDSS.