first of all  only in aniline and benzoic acid o-effect is applicable

any grp like EDG OR EWG on ortho position of aniline or benzoic acid increses acidic strengh

so aniline with methyl group on ortho position will be more acidic than aniline

therfore aniline is more basic than anline with methyl grp on ortho position

so ans is 1

i dont think there will be any steric hinderence

hope u understood the explaination

pls tell me whther i am wrong