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Scuola San Giovanni Evangelista's Secret?
You're right that it isn't a school, but there's a wrinkle worth knowing: the confraternity ran a hospital and a burial duty for condemned prisoners, and members accompanied the condemned to the gallows at Campo de' Fiori and Ponte Sant'Angelo. That's the actual grim thread running through the place, not hidden libraries. If you want the confraternity-with-a-dark-job angle made visible, the Chiesa di San Giovanni Decollato near the Bocca della Verità is the one to see. Same charitable-and-macabre tradition, and its frescoes by Jacopino del Conte actually show the executions the brothers attended.
Worth knowing that the building isn't really open as a visitable monument. It's tied to the Arciconfraternita di San Giovanni Evangelista and mostly opens for their own functions, so you can't just wander in looking for passages. Your best shot is the annual open days during the Settimana della Cultura, usually in spring, when a lot of these locked oratories unlock their doors. For the grandma vibe with actual access, the Oratorio del Gonfalone on Via del Gonfalone does guided tours and has that same confraternity feel with frescoes you can stand right in front of.
Worth knowing that the building sits on what was once the Vicus Sandaliarius, an ancient street where sandal makers worked. Excavations around there turned up Roman shop remains, so the "hidden rooms" under these confraternity oratories are often just the older city still sitting there. My honest take, though, is that the ivy and stone you saw online is mostly a facade thing, and the interior is a single barrel vaulted hall, not a warren of passages. If your grandmother's Naples stories are what hooked you, spend your time at the Chiesa di Sant'Agnese in Agone or poke around the basements of San Clemente, where the layered history is actually visible to visitors.
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What are current tobacco prices for LM Blue or Chesterfield Blue?
tbh duty free at Riga is only worth it if you're buying cartons, single packs at the airport arent that much cheaper than teh tabaccai in Rome. also remember you can only bring a limited amount into the EU anyway so stockpiling has its limits
Chesterfield Blue usually runs around 5.50 to 6 euros a pack in Rome these days, though tabaccai prices are fixed by the state so it won't vary much shop to shop. Riga is generally cheaper for cigarettes but your layover time matters, if it's tight you might not have time to clear security and find a shop.
LM Blue in Rome is roughly the same ballpark, around 5.50 to 6 euros. One thing to keep in mind at Riga airport, the duty free selection isn't always great for specific brands like these, so if you're set on LM or Chesterfield you might strike out. I'd check what the actual duty free has before counting on it.