A couple of things... First, I don't think you will find a winter barley that will over winter with any kind of repeatability in NW WI. I haven't seen one work in SE WI. Maybe there is something out there...
2nd, most cereals don't like wet feet, so it may be a challenge no matter what you pick.
3rd, I've fed both winter wheat and barley (and of course corn) to high producing dairy cows, and either will work. I grind wheat 1000 bu at a crack and store it ground for a month, and have never had issues with rancidity- it kept great. Both wheat and barley have faster digesting starch than corn- more like high moisture corn or faster, depending on the grind. The finer, the hotter it is. I've prefer wheat over barley... just as good of feed, and probably 50% more feed per acre. (Barley is, I think, 44 or so lb per bu, wheat is 60). The only warning with wheat is don't go over 5-6 lb per day, as the wheat flour can form a sticky rising mess in the rumen, just like rising bread. FYI, I see a protein test jjump feeding wheat over corn.
If you have a grass issue, the wheat would be better as it would try to crowd it out in the spring. Barley (at least the spring kind) is not nearly as thick. Conversely, trying to put seeding under wheat is difficult for the same reason- it can choke it out.
Why not burn the field off with roundup now, and seed it now to clover? No till seeding is very successful. I think you would have ample time for establishment yet. Here we can seed alfalfa successfully until Labor day, and clover later.
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