We investigate potential systematic effects in constraining the amplitude of primordial fluctuations sigma_8 arising from the choice of halo mass function in the likelihood analysis of current and upcoming galaxy cluster surveys. We study the widely used N-body simulation fit of Tinker et al. (T08) and, as an alternative, the recently proposed analytical model of Excursion Set Peaks (ESP). We first assess the relative bias between these prescriptions when constraining sigma_8 by sampling the ESP mass function to generate mock catalogs and using the T08 fit to analyse them, for various choices of survey selection threshold, mass definition and statistical priors. To assess the level of absolute bias in each prescription, we then repeat the analysis on dark matter halo catalogs in N-body simulations designed to mimic the mass distribution in the current data release of Planck SZ clusters. This N-body analysis shows that using the T08 fit without accounting for the scatter introduced when converting between mass definitions (alternatively, the scatter induced by errors on the parameters of the fit) can systematically over-estimate the value of sigma_8 by as much as 2sigma for current data, while analyses that account for this scatter should be close to unbiased in sigma_8. With an increased number of objects as expected in upcoming data releases, regardless of accounting for scatter, the T08 fit could over-estimate the value of sigma_8 by ~1.5sigma. The ESP mass function leads to systematically more biased but comparable results. A strength of the ESP model is its natural prediction of a weak non-universality in the mass function which closely tracks the one measured in simulations and described by the T08 fit. We suggest that it might now be prudent to build new unbiased ESP-based fitting functions for use with the larger datasets of the near future.