Update:
I think I got this now...
Pretty sure these buildings are the same (Crescent Billiard Hall) for the reasons shown (support pole and railing style):
So that means the streetcar station is probably the small building next to the streetcar loop:
Something I was thinking previously but needed a link. Now I have one. I will note that there is no X on the robbery map at this location so maybe this is a completely different heist.
And as for the previously mentioned Fontana Theatre I may have found the inspiration for that right where we were already looking. There is a structure very similar to it next to the billiards hall just like in-game:
^On the left https://www.google.com/maps/@29.9526961,-90.0694841,3a,75y,301.53h,125.3t/data=!3m6!1e1!3m4!1swch1MQmADknR0fBiAGamqA!2e0!7i13312!8i6656
The place in real life is 119 St Charles Ave. Formerly "The Pearl Restaurant and Oyster Bar". The in-game structure does not have balconies, though.
And while trying to find more historical photos of the place, I found this drawing that shows the building in question was a lot shorter way back when (unknown date, but the columned building was detroyed by fire in 1894):
^Billiard hall on the right.
edit: wiki has a photo of the same circa 1885-1894:
It had more floors in 1910, though (far right barely in view):