Stellar evolution models of massive stars are very sensitive to the adopted mass-loss scheme. The magnitude and evolution of mass-loss rates significantly affect the main sequence evolution, and the properties of post-main sequence objects, including their rotational velocities. Driven by potential discrepancies between theoretically predicted and observationally derived mass-loss rates in the OB star range, we particularly aim to investigate the response to mass-loss rates that are lower than currently adopted, in parallel with the mass-loss behavior at the first bi-stability jump. We perform 1D hydrodynamical model calculations of single $20 - 60 , M_{odot}$ Galactic ($Z = 0.014$) stars where the effects of stellar winds are already significant during the main sequence phase. We develop an experimental wind routine to examine the behavior and response of the models under the influence of different mass-loss rates. This observationally guided, simple and flexible wind routine is not a new mass-loss description but a useful tool based on the Wind-momentum Luminosity Relation and other scaling relations, and provides a meaningful base for various tests and comparisons. The main result of this study indicates a dichotomy when accounting for currently debated problems regarding mass-loss rates of hot massive stars. In a fully diffusive approach, and for commonly adopted initial rotational velocities, lower mass-loss rates than theoretically predicted require to invoke an additional source of angular momentum loss (either due to bi-stability braking, or yet unidentified) to brake down surface rotational velocities. [...]