Measuring the HI-halo mass scaling relation (HIHM) is fundamental to understanding the role of HI in galaxy formation and its connection to structure formation. While direct measurements of the HI mass in haloes are possible using HI-spectral stacking, the reported shape of the relation depends on the techniques used to measure it (e.g. monotonically increasing with mass versus flat, mass-independent). Using a simulated HI and optical survey produced with the SHARK semi-analytic galaxy formation model, we investigate how well different observational techniques can recover the intrinsic, theoretically predicted, HIHM relation. We run a galaxy group finder and mimic the HI stacking procedure adopted by different surveys and find we can reproduce their observationally derived HIHM relation. However, none of the adopted techniques recover the underlying HIHM relation predicted by the simulation. We find that systematic effects in halo mass estimates of galaxy groups modify the inferred shape of the HIHM relation from the intrinsic one in the simulation, while contamination by interloping galaxies, not associated with the groups, contribute to the inferred HI mass of a halo mass bin, when using large velocity windows for stacking. The effect of contamination is maximal at Mvir~10^(12-12.5)Msol. Stacking methods based on summing the HI emission spectra to infer the mean HI mass of galaxies of different properties belonging to a group suffer minimal contamination but are strongly limited by the use of optical counterparts, which miss the contribution of dwarf galaxies. Deep spectroscopic surveys will provide significant improvements by going deeper while maintaining high spectroscopic completeness; for example, the WAVES survey will recover ~52% of the total HI mass of the groups with Mvir~10^(14)Msol compared to ~21% in GAMA.
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