Alcoholic potassium permanganate for oxidation
Practical considerations, mainly that toluene is non-polar, inorganic. Aqueous $\ce{KMnO4}$ wouldn't be miscible so the oxidation can only take place in the interface. By using alcoholic $\ce{KMnO4}$, we can get the $\ce{KMnO4}$ into the organic layer much more easily, thus making the reaction much faster.

To form an ester, you generally need a dehydrating environment. Plus, the oxidation of toluene with $\ce{KMnO4}$ in neutral conditions will produce base which neutralizes the benzoic acid, thus deactivating it making it unable to undergo esterification.