Various interesting characters all hang out at a local watering hole on a tropical beach. Series of quasi-independent stories all tie in to that beach bar.
It is NOT The Tugboat Man by D. T. Iverson.
It is not The Shack by Todd d172. Correction, might be: I read the first & last stories in the Shack Universe and there was no mention of a beach bar.) I need to reread as I see that #2 takes place in & around a beach bar.
If you know of other similar stories about beach bums, feel free to list them.