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If I'm not mistaken, achievements only work in single player. Not sure if that's the cause of you not being awarded achievements? I also doubt if work during contracts count. Could very well be you need to work on your own fields for the 100 hectares achievements. I think AI helper counts though.
That has me thinking, I do most of my field work with Courseplay. Maybe the game isnt registering? Stats page does show over 100 ha harvested though.
https://steamcommunity.com/stats/787860/achievements/