We investigate the performance of three different data-driven prognostic methodologies towards the Remaining Useful Life estimation of commercial aircraft brakes being continuously monitored for wear. The first approach utilizes a probabilistic multi-state deterioration mathematical model i.e. a Hidden Semi Markov model whilst the second utilizes a nonlinear regression approach through classical Artificial Neural Networks in a Bootstrap fashion in order to obtain prediction intervals to accompany the mean remaining life estimates. The third approach attempts to leverage the highly linear degradation data over time and uses a simple linear regression in a Bayesian framework. All methodologies, when properly trained with historical degradation data, achieve excellent performance in terms of early and accurate prediction of the remaining useful flights that the monitored set of brakes can safely serve. The paper presents a real-world application where it is demonstrated that even in non-complex linear degradation data the inherent data stochasticity prohibits the use of a simple mathematical approaches and asks for methodologies with uncertainty quantification.