Keep in mind that what works for one - might fail for you -
The soil - climate and terrain have a lot to do with everything.

Generally up north -

Clovers are tough to beat to start with for year round activity-
Soybeans Can be great summer/fall and even winter if you plant enough
Corn is king in winter

With nothing to back up my Opinion - In MD - I like Soybeans Summer-Winter - especially if not everyone one around you is planting them.

With 12 acres to work with - I'd plant a variety and let me observations lead me on.

FH