Cap'n Mark,
A perfect topic in these days before Halloween!
I recall studying these gravestone motif's years ago as I was researching many markings and motif on 17th and 18th century swords, mostly hangers and such. The appearance of cherubs and figures of heads (not necessarily death heads ) occur on various hilts, as well as 'the Green Man'. The famed 'Mortuary' swords supposed to represent the death head of Charles I during the Civil Wars in England were actually around before his death, so that 'lore' not really accurate.
The skull and crossbones as a symbol of death were around long before pirates, and were indeed sometimes placed in or around cemeteries .
With the Masonic connection it does not seem a widely present 'brotherhood' in Europe until the 18th century, but of course there were some connected groups before then (they hardly appeared suddenly).
The skull and crossbones represent the 'memento mori' (remember that you too shall die) often used in Masonic ritual and symbolism.
I have understood that from a maritime theme, in ships logs, a sailor deceased often had the skull and crossbones next to his name. As many 'pirates' had come from these naval ranks and become 'outlaw', they saw themselves as 'dead' to their former world, and now 'on account'.
As Mark has said, the deaths head (skull) and crossbones, the fabled 'Jolly Roger" was hardly the only pattern or configuration used on the flags flown by pirates. Also present were the hourglass, the scythe or skeletons with them, hearts and other unusual symbols.
Getting to the gravestones, the deaths head with wings symbolized the spirit flying to the next world or to that effect. These kinds of rather morbid symbols gave way to cherubs and angels and other lighter figures with Biblical associations of classical nature in just prior to mid 18th c. .
However, there were always those very 'old school' and so many headstones often still carried the old symbols.
As Mark noted, pirates were hardly required to stay close to the ocean, and often strayed far inland, and many of their vessels were smaller and shallow draft which could navigate many Eastern rivers.
The presumption of these skull and crossbones on headstones or in general as distinctly announcing the presence of a pirate is hardly unusual. It has become so firmly emblazoned in folklore it is an almost expected reaction.
Also, would not a pirate who had not committed a capital act, and who was executed, in effect have paid his debt to society, and not necessarily be denied redemption in the afterlife? hence the words, God have mercy on his soul.
As far as I have known, criminals, suicides and such were indeed often buried in unmarked graves, but in locations outside established cemetery parameters or even further out in so called 'Potters Fields'. There were other divisions in burial compatibility, such as the dead of opposing forces in battles etc. or as noted slaves or Native American groups not mingled with others in set cemeteries.
As far as unnamed headstones, it would seem unlikely that anyone of the mentioned groups would be placed among other locals in a cemetery, and unusual even to have a headstone at all. It is possible, as noted, that family of a pirate might retrieve the body and bury it not to be found out, but that seems tenuous at best.
I don't think plague victims would have unmarked stones, as many have their names and died of 'whatever malady' marked without abandon.
With the medical notions of the times I think that burial would suffice as far as keeping contagion in check, and as victims they had no transgression to place them otherwise.
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