We investigate the quality of associations of astronomical sources from multi-wavelength observations using simulated detections that are realistic in terms of their astrometric accuracy, small-scale clustering properties and selection functions. We present a general method to build such mock catalogs for studying associations, and compare the statistics of cross-identifications based on angular separation and Bayesian probability criteria. In particular, we focus on the highly relevant problem of cross-correlating the ultraviolet Galaxy Evolution Explorer (GALEX) and optical Sloan Digital Sky Survey (SDSS) surveys. Using refined simulations of the relevant catalogs, we find that the probability thresholds yield lower contamination of false associations, and are more efficient than angular separation. Our study presents a set of recommended criteria to construct reliable cross-match catalogs between SDSS and GALEX with minimal artifacts.