Ok so I get that you need to go into workshop mode and select a person to harvest crops... But do I need to keep assigning the same person to keep harvesting... because it seems like if I don't keep doing it manually it doesn't seem to get done...

They don't actually harvest it, the game just counts the plants and which plants they are(which only comes into play if you have a food surplus). Basically the game never actually harvests the plants just add food to the workshop based on how many there are, and if there is a food surplus you can find food items based on which crops you've planted in the workshop.

From my experience you don't have to assign them to crops they will do this automatically if they don't have another assignment. And yah, they don't actually harvest the crop (as in remove the corn from the stalk). As long as the screen shows your food count correctly in the workshop menu, they are "harvesting them" 1 person can only "harvest" 6 crops at a time though. So if your food needs to be 7. You need two people assigned to a crop. You don't have to assign them individually to each crop, the AI will have them harvest up to 6 if you have that many.

Now I'm not 100% on this just going off of what the game has said and what I've seen. What is interesting though, is that some crops are only worth .5 food and Im not sure if the AI recognizes that 1 Food=1 harvested crop or if its 1 crop harvested, whether its worth .5 Food or 1 Food from said crop.

I think for the automatic harvesting, the crops have to be close to each other. Mutfruit is the only one I've seen that counts as 1 rather than .5, and wild mutfruit cannot be planted. So it's going to take a little manual picking and replanting to get those numbers up, once you find a mutfruit.

One person can work 6 food items worth of crops. That means 12 plants when each gives 0.5 food. You also don't have to assign them individually. Assign him one an he will work on all plants nearest to him he can. You can confirm that by watching food stat changing while in building mode.

I hope they'll patch in automatic assignments.. micromanaging several settlements is downright stupid. Especially because there's no means to see who is assigned to what (assign generic settler #43 that looks just like every other settler to a shop and you'll suddenly lose food cause you had previously assigned him there). Also, in some places, it's difficult to even find all the settlers without using the bell.

I think you could expect even the most stupid of settlers to decide by themselves to take on a job that is not currently assigned without the hero of the wasteland taking him by the hand and shoving his face in it.

When you mouseover settler in building mode, all structures/crops he is assigned to are highlighted.

Doesn't help any if they're not near them.

It feels like whoever designed the settlement mode has absolutely zero experience with any kind of building games like that and ignored all the basics that make for a usable interface.

Give than time to polish things. It's first time they implemented something like that and it's quit a huge addition requiring lot of work.