The server should be one big medieval city, and you choose one job (using the jobs plugin) and you are given a plot, deed ,and resources to start your business.
For example: If a new player joins they immediately have options for jobs. Let's say the player decides he is a good blacksmith, he would be teleported to an unowned blacksmith shop and the player would receive a deed and the shop. The player can not destroy the shop but use the equipment (By equipment I mean a furnace and coal) inside to become a proper blacksmith. The blacksmiths job would be to smelt ores at a set price per piece. Some jobs would come with equipment you need. An example of this is a guard, if the guard doesn't have the equipment (Armor and a sword) then citizens are not going to respect the guard as much or be as law abiding.
Also, you should be able to become a settler and create new colonies.
Just a Suggestion...
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