Constitutional and conformational isomers of bromopropanol are vibrationally and rotationally characterised with parallels drawn to the structural chlorine analogues. A previous microwave spectroscopic study of the chloropropanols is re-examined and all systems are explored by Raman jet spectroscopy. For bromine, the entire nuclear quadrupole coupling tensors are accurately determined and compared to their chlorine counterparts. Tensor asymmetry parameters are determined and linked with the hydrogen bond strength as indicated by the downshift of the OH-stretching frequency. The spectroscopic constants derived from the observed transitions are used as benchmarks for a large variety of electronic structure methods followed by harmonic and anharmonic rovibrational treatments. The CCSD(T) electronic structure calculations provide the best performance, in particular once anharmonic and relativistic corrections are applied or implied. Standard DFT approaches vary substantially with respect to their systematic error cancellation across the investigated species, and cost-effective compromises for the different observables are proposed.