3-step process to make propyl ethanoate from propene
My proposal is hydroboration followed by Fischer esterification. It's 2 or 3 steps depending on how many you count hydroboration to be.



Alternatively if you are intent on going through a haloalkane pathway, you could try anti-Markovnikov addition of $\ce{HBr}$ by reacting it in the presence of $\ce{H2O2}$ to prepare 1-bromopropane. Then you could do nucleophilic substitution of $\ce{OH-}$ followed by Fischer esterification. This method would have a lower yield though due to the competing E2 reaction.