Manipulating light by adding and subtracting individual photons is a powerful approach with a principal drawback: the operations are fundamentally probabilistic and the probability is often small. This limits not only the fundamental scalability but also the number of operations that can be applied in realistic experimental settings. We propose and analyze a loop-based technique which can significantly increase the probability of success while preserving the quality of the photon subtraction. We show the improvement both in single mode preparation and manipulation of non-Gaussian states with negative Wigner functions and in two-mode entanglement distillation protocol with Gaussian states of light.