I now have all done except lumberers are only at 2, and I spent a whole game day following them around and they just laze about doing nothing.
Whatcha Jameser - Following them round is a bad thing, I found the more I hung around the less they wanted to work. Same for the farmers, the doctor etc. The best way I found was run around the Homestead getting as many you can, leave and do some hunting or a mission until at least a day has passed in game and then return and scan them again. Doing it this way seemed far quicker than watching him fix that stupid wheel or fish all the time.
Also as a side note any of the workers can be scanned playing bowls next to the Inn, this was how I finished Doctors and Lumberers. I haven't tried this post update however.