I know I'm just wrong about this but I'd appreciate some help seeing why. It seems to me like the phenol proton in salicylic acid should be more acidic than the carboxyl proton. When I try to draw resonance structures for the conjugate base, it looks to me like the charge gets distributed over two oxygen atoms and the whole ring (if anyone can tell me what software makes the nice pictures in some answers here I'd take it):
Then when I try to draw the conjugate base when the carboxyl group is deprotonated, as far as I can tell only the oxygens take the charge, and trying to distribute over the ring results in invalid resonance structures because you aren't supposed to add formal charges to already charged species.
What am I doing wrong?