Using N-body simulations we study the impact of various systematic effects on the bulk flow (BF) and the Cosmic Mach Number (CMN). We consider two types of systematics: those related to survey properties and those induced by observers location in the Universe. In the former category we model sparse sampling, velocity errors, and survey incompleteness. In the latter, we consider Local Group (LG) analogue observers, placed in a specific location within the Cosmic Web, satisfying various observational criteria. We differentiate such LG observers from Copernican ones, who are at random locations. We report strong systematic effects on the measured BF and CMN induced by sparse sampling, velocity errors and radial incompleteness. For BF most of these effects exceed 10% for scales $Rleq100h^{-1}$Mpc. For CMN some of these systematics can be catastrophically large ($>50%$) also on bigger scales. Moreover, we find that the position of the observer in the Cosmic Web significantly affects the locally measured BF (CMN), with effects as large as $sim20%$ ($30%)$ at $Rleq50h^{-1}$Mpc for a LG-like observer as compared to a random one. This effect is comparable to the sample variance. To highlight the importance of these systematics, we additionally study a model of modified gravity (MG) with $sim15%$ enhanced growth rate. We found that the systematic effects can mimic the modified gravity signal. The worst-case scenario is realized for a case of a LG-like observer, when the effects induced by local structures are degenerate with the enhanced growth rate fostered by MG. Our results indicate that dedicated constrained simulations and realistic mock galaxy catalogs will be absolutely necessary to fully benefit from the statistical power of the forthcoming peculiar velocity data from surveys such as TAIPAN, WALLABY, Cosmic Flows-4 and SKA.