A good Morrowind reference would be the LGNPC Pelagiad mod, which let you work for Mebestien Ence. Does anything like this exist for Oblivion?
I know this isn't exactly what you're looking for, but Valley View Estate has some of this factor. You go through a short questline and get this estate. You hire folks to work the vineyard and to guard it. Your folks work the vineyard and produce wine. If you age the wine in your wine cellar, you can take it and sell it to a travelling vendor. A nice way to make some money but once it's set up you only go back once every ten days to pick up the aged wine, and pay your folks. You could rp there but can't really make the wine yourself. Anyway it's a good one to have for a business running mod.