sandy mortar means its time to repoint,,, n-bor across the st had the same trouble & blamed her roofer 'cause of wtr inside the living room's fireplace,,, the problem was sandy mortar - we repointed & it was solved,,, sealed w/prosoco's ( no financial interest - the supplier's just the closest to us ) silicone siloxane a month later.
you already know about the flashing stuff & retro-fitting is expensive,,, we still use sheet lead & plugs - NEVER caulk/roofing cement/silicone sealant.
ps - old bricks hate modern mortars as you probably also know
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