Would sodium salicylate dissolve in HCl? I've been searching around the web and the consensus seems to be sodium salicylate dissolves poorly in HCl because it would form salicylic acid. However, I don't understand why forming salicylic acid product (which is poorly soluble in water) would make sodium salicylate (which is the reactant) dissolve poorly in HCl. If HCl doesn't contribute to making it more soluble, wouldn't the polarity of the water molecule dissolve it anyway?
HCl is in almost all cases already aqueous for common chemistry, mostly dissociated into $\ce{H^+} + \ce{Cl^-}$ because it is a strong acid, which means water is the primary solvent, not HCl. Pure HCl under ambient conditions is actually a gas (thus certainly not a pure liquid solvent).

That leaves the compound in question insoluble in the water after being protonated by $\ce{H^+}$ to form the insoluble acid molecule.

The process I mentioned in the comment is illustrated here: