The advent of new multichromophoric systems capable of undergoing efficient intramolecular singlet fission (iSF) has greatly expanded the range of possible motifs for multiexciton generation approaches for organic light energy harvesting materials. Transient absorption (TA) spectroscopic probes are typically used to characterize singlet fission processes that may place limitations on sensitivity and time resolution on scales comparable to the full lifespan of spin-forbidden triplets and interactions. Here, we investigate the ability of fluorescence-based spectroscopic probes to detect iSF activity in isolated dyads based on large substituted conjugated acenes (e.g., tetracene and pentacene derivatives). Photophysical models are simulated from several iSF-active dyad systems reported in the literature using a stochastic approach to assess the sensitivity of steady-state fluorescence to the presence of triplet excitons. The results demonstrate large fluctuations in expected fluorescence yields with varying excitation rate constants for systems with Phi(iSF) > 0.5 (assuming weak interchromophore coupling). Exciton-exciton interactions are also investigated, and we further demonstrate how treating iSF dyads stochastically (i.e., finite number of chromophores) accentuates dependences of photophysical yields with excitation rates. Last, our approach reveals the potential ability of single molecule level fluorescence spectroscopy to detect iSF activity that can aid efforts to design and optimize candidate iSF systems.