We study failure rate monotonicity and generalized convex transform stochastic ordering properties of random variables, with a concern on applications. We are especially interested in the effect of a tail weight iteration procedure to define distributions, which is equivalent to the characterization of moments of the residual lifetime at a given instant. For the monotonicity properties, we are mainly concerned with hereditary properties with respect to the iteration procedure providing counter-examples showing either that the hereditary property does not hold or that inverse implications are not true. For the stochastic ordering, we introduce a new criterium, based on the analysis of the sign variation of a suitable function. This criterium is then applied to prove ageing properties of parallel systems formed with components that have exponentially distributed lifetimes.