I just checked Naples population. As of 2018 the pop is 19537. I’m going to assume the pop was much less in 1923 — 3000-5000 maybe? So if Michael’s Little Club was open in 1923 I’d say there is a good chance chips sent to Naples Little Club, Naples, Fl were in fact sent to Michael’s who had a poker room named Naples Little Club. Just a thought

You said the club ws opened to at least 1920. Maybe it was still n in 1923?