Probing the transition dipoles responsible for the luminescence of a nanoemitter is essential to understanding its physical properties, its interactions with its environment, and its potential applications. Various methods in photoluminescence microscopy, based on polarimetry or Fourier imaging, have been developed to measure an emitter's dipole properties: the number of radiating dipoles, the oscillator strength ratio between them, and their orientation. In this article, we model the most used of these protocols and show that their sensitivity depends crucially on the experimental conditions: substrate material, presence of another lower or upper layer, and objective numerical aperture. We develop guidelines to optimize the measurement sensitivity by tailoring the experimental conditions, depending on the type of protocol used and the dipole property to be measured.