halfling as gypsies makes sense
Back before 3.0, I was working on my D&D campaign and trying to find a niche for each of the PC races that were in keeping with the racial sterotypes already present in 1st and 2ed, but with a twist to make my home campaign setting somehow distinctive.
When thinking about the qualities that seemed to typify D&D halflings, I settled on the apparently contradictory traits of "homebodies who like consistency and a simple rural lifestyle" a holdover from their tolkien origins and the "adventurous and clever, with some mild larcenous tendencies" halflings of the D&D mythos. The solution to melding these two opposites concepts came to me in an epiphany: gypsies! How else could a people enjoy the comforts of home and a simple rural lifestyle and yet be adventurous and slightly larcenous?
In my campaign, halflings are are race of nomadic wandering tinker/entertainers who travel in caravans called "companias" of brightly painted wagons. Each compania consists of one or two large extended families. Each compania practices a particular trade that they can perform barter for supplies in villages as they travel endlessly about the land. Some families are renowned instrument makers, glassblowers, cobblers, carpenters, blacksmiths, ect. A few companias are even renowned performing troupes.
Imagine my surprise when 3.0 presented halflings as gypsies! When I considered however, it seemed likely that the game designers had followed the same train of thought as I and had reached the same conclusions. What better adventurous niche than gypsies for the halflings to occupy in D&D?
