Multiple gravity assist (MGA) spacecraft trajectories can be difficult to find, an intractable problem to solve completely. However, these trajectories have enormous benefits for missions to challenging destinations such as outer planets and primitive bodies. Techniques are presented to aid in solving this problem with a global search tool and additional investigation into one particular proximity operations option is discussed. Explore is a global grid-search MGA trajectory pathsolving tool. An efficient sequential tree search eliminates v∞ discontinuities and prunes trajectories. Performance indices may be applied to further prune the search, with multiple objectives handled by allowing these indices to change between trajectory segments and by pruning with a Pareto-optimality ranking. The MGA search is extended to include deep space maneuvers (DSM), v∞ leveraging transfers (VILT) and low-thrust (LT) transfers. In addition, rendezvous or nπ sequences can patch the transfers together, enabling automatic augmentation of the MGA sequence. Details of VILT segments and nπ sequences are presented: A boundaryvalue problem (BVP) VILT formulation using a one-dimensional root-solve enables inclusion of an efficient class of maneuvers with runtime comparable to solving ballistic transfers. Importantly, the BVP VILT also allows the calculation of velocity-aligned apsidal maneuvers (VAM), including inter-body transfers and orbit insertion maneuvers. A method for automated inclusion of nπ transfers such as resonant returns and back-flip trajectories is introduced: a BVP is posed on the v∞ sphere and solved with one or more nπ transfers – which may additionally fulfill specified science objectives. The nπ sequence BVP is implemented within the broader search, combining nπ and other transfers in the same trajectory. To aid proximity operations around small bodies, analytical methods are used to investigate stability regions in the presence of significant solar radiation pressure (SRP) and body oblateness perturbations. The interactions of these perturbations allow for heliotropic orbits, a stable family of low-altitude orbits investigated in detail. A novel constrained double-averaging technique analytically determines inclined heliotropic orbits. This type of knowledge is uniquely valuable for small body missions where SRP and irregular body shape are very important and where target selection is often a part of the mission design.