Theres definitely better solvent to use other than pyridine. You do need a base to neutralize the acid but the correct base would also help convert any remaining psilocybin to psilocin and start the reaction by breaking the AA apart. Im working on an sop straight from extract thats based off my cannabinoid acetylation sop. I do not plan on making the freebase though.
This explains some of the chemistry behind my sop