New rotorcraft configurations are emerging, such as the optimal speed helicopter and slowed-rotor compound helicopter which, due to variable rotor speed and redundant lifting components, have non-unique trim solution spaces. The combination of controls and rotor speed that produce the best steady-flight condition is sought among all the possible solutions. This work develops the concept of optimal rotorcraft trim and explores its application to advanced rotorcraft configurations with non-unique, constrained trim solutions. The optimal trim work is based on the nonlinear programming method of the generalized reduced gradient (GRG) and is integrated into a multi-body, comprehensive aeroelastic rotorcraft code. In addition to the concept of optimal trim, two further developments are presented that allow the extension of optimal trim to rotorcraft with rotors that operate over a wide range of rotor speeds. The first is the concept of variable rotor speed trim with special application to rotors operating in steady autorotation. The technique developed herein treats rotor speed as a trim variable and uses a Newton-Raphson iterative method to drive the rotor speed to zero average torque simultaneously with other dependent trim variables. The second additional contribution of this thesis is a novel way to rapidly approximate elastic rotor blade stresses and strains in the aeroelastic trim analysis for structural constraints. For rotors that operate over large angular velocity ranges, rotor resonance and increased flapping conditions are encountered that can drive the maximum cross-sectional stress and strain to levels beyond endurance limits; such conditions must be avoided. The method developed herein captures the maximum cross-sectional stress/strain based on the trained response of an artificial neural network (ANN) surrogate as a function of 1-D beam forces and moments. The stresses/strains are computed simultaneously with the optimal trim and are used as constraints in the optimal trim solution. Finally, an optimal trim analysis is applied to a high-speed compound gyroplane configuration, which has two distinct rotor speed control methods, with the purpose of maximizing the vehicle cruise efficiency while maintaining rotor blade strain below endurance limit values.