A useful source for this is Ælfric's Colloquy, a Latin textbook for novices from 10th Century England. Written by Ælfric of Eynsham, also famous for his homilies, the Colloquy is somewhat like a modern phrasebook, insofar as it is presented as a series of conversations - colloquies - written in both Latin and Old English. The format of the textbook is a series of conversations between the boys and their teacher, and the various figures that they encounter while walking through their community. Each of the people they encounter then explains to the class what they do, and how their job is important, before they all agree to go off and get drunk.

500 people would be a relatively large community, probably some 80-100 households as settlements were typically accounted for, so many if not all of the roles are likely to have been encountered. Bear in mind, of course, that the figures encountered in 10th Century England are not necessarily the same as would definitely be found in, say, 14th Century Burgundy, or even 12th Century England. The hunter in Ælfric's 10th century conversation would have likely fallen foul of the forest laws a century later; not that people stopped hunting, of course, but they'd have to be far more circumspect about it.

In chronological order, the figures encountered in the Colloquy are: a ploughman, a shepherd, an oxherd (likely in later centuries to be a hostler instead), a hunter of deer, boar and hares, a fisherman, a birdcatcher and hawker, a merchant, a tanner, a salter, a cook, a lawyer, a blacksmith and a carpenter.

Other figures that would be likely fixtures of a community would be a miller, who either made a living directly from multure, or claimed a salary from the land owner, and of course the general agricultural labourer. Women would have been employed largely in the spinning of wool and the weaving of yarn into cloth. In a larger community, it's likely that there would also have been some sort of doctor, or at least a community figure with knowledge of herbology and some medical skills, who may also have doubled as a midwife. And of course, at least within Western Europe, there would be a priest.