Hi, you don’t say if your land is going to be trampled by the machinery, and so the plants too. Also you don’t tell us if the land is dry or wet.
Some suggestions to maybe think about – it’s where I’d start.
Wet ground – flag Iris – they die down in winter so that could be a good time to allow the machinery across.
– willow – I know it’s woody but every autumn, if you pick the right variety, it could give you whips for basketry, a crop and an effective windbreak but not over winter. The same with flag iris of course.
Ordinary ground – Tall grasses, intersperse with wildflowers – tall ones of course – if the area is big enough may be able to have a bee hive, if not could be beneficial to a host of insects. Get into good books with local farmer to graze if necessary. A bit of winter windbreak if only grasses of course.
Bamboos – edible and you have a crop, if the machinery doesn’t go over your land then these could be an option and would be an effective windbreak year round.
Grasses like Yucca or New Zealand flax – good windbreaks when mature but maybe machinery couldn’t get through them.
Jerusalem artichoke only really supplies a windbreak for me from July to October – not when I’d need one. Comfrey dies down early too.
Other ideas: – Temporary plantings to grow on before potting up if running a nursery.
Does it have to be a windbreak – plant quick growing crops, or crops which need the time between the machinery coming and going.
Sunflowers – maybe the perennial maximillian type.
Hope this gives some ideas.