RE: Winter wheat.. brassicas, clover??
For me - Rye has always been the easiest.
Plant in Sept. 1st in the North - and as long as the snow is less than 1 ft - the deer will use it well.
as long as you can bare the soil - you can get it to grow. Winter Wheat is similar but in my experience doesn't germinate as easily and the soil has to be a little better,
FH