Should be quite easy by performing an acidic esterification catalyzed by H2SO4 in MeOH under reflux over night. There you usually get 98 % conversions.
I do not think it necessary to get 100% conversion of salicylic acid. In addition to the conversion, the reaction time is important (esterification is a slow reaction). Moreover, methyl salicylate has a high boiling point and is difficult to dissolve in water. If the catalyst is to be H2SO4, it is worth mixing it with alcohol beforehand. Regards,