Malic acid 3-step synthesis
I have clarified with my chemistry tutor and it appears that performing the substitution and the addition as two separate steps with two separate sets of conditions is absolutely necessary. The most important reason would be the temperature, which is also the most stark difference between the two different set of conditions.

Due to entropy considerations, addition should ideally be carried out at low temperatures. Thus, if we would like to have the addition of $\ce {HCN}$ to the substrate, it should be done at much lower temperatures as the reaction has a negative entropy change. However, the substition of $\ce {Br}$ by $\ce {CN}$ does not need such low temperlatures and should be done at higher temperatures to provide enough energy of activitation to break the carbon-bromide bond.