![o-Toluidine][1] 
![o-Toluic Acid][2]


[1]: https://i.sstatic.net/IrZpvs.png  
[2]: https://i.sstatic.net/nlLYys.jpg

When comparing o,m,p-toluidine, basicities, *ortho effect* is stated as a reason why o-toluidine is weaker But, When comparing o,m,p-toluic ccid basicities, *ortho effect* is stated as a reason why o-toluic acid is stronger acid.  Further, I was given the definition that *ortho effect* is an effect in which an ortho- group causes steric hindrance, forcing the $\ce{-COOH}$ or $\ce{-NH2}$ or some other bulky group to move  out of the plane, inhibiting resonance. Then, if ortho effect inhibits resonance, why is o-toluic acid the strongest and o-toluidine the weakest?
  
Where am I going wrong in my understanding of the ortho effect?