While I find the concept of RPG generators as handy, I never use them. Basically I'd come up with a list of likely crafters and merchants at the most basic level, what one must find in the smallest of communities, then progressively add occupations based on larger populations and rarity in the lowest populations that increases in commonality in larger groups. Then I'd look at geography or nearness to specific resources, by the ocean means more sea industry, being near the forests or mountains means more woodcutters, hunters and the like, or more rural, thus more agricultural related occupations. Look at what you'd consider as most basic altered for each geographic type.
Once you have a set of lists, use them as tables to roll up your communities by occupation.
I know that sounds like lots of work, but you have an interesting dilema and that's just a part of world building. It would be a useful exercise just trying to create a realistic occupations "generator" to do by hand.