Looking at your photos I think the trees might be Austrian pine not red pine. If you could send more picture of the foliage and if possible the cones. We can verify which pine it is. 

If it is Austrian pine I think your are seeing the symptoms of Dothistroma needle blight and Diplodia tip blight. Dothistroma needle blight  first appears as dark green, water-soaked spots on the needles. The spots become tan, yellow, or reddish-brown, and may encircle the needles to form bands. The tip of the needle beyond the band eventually dies leaving the base of the needle alive and green. The Diplodia tip blight fungus kills the current year shoots and sometimes branches.

Here are links to more information on both of these diseases.

Dothistroma needle blight - https://extension.umn.edu/plant-diseases/dothistroma-needle-blight

Diplodia tip blight - https://extension.umn.edu/plant-diseases/diplodia-shoot-blight-and-canker

Those are red pine cones. I am not sure what is turning the needles brown/flecking. I think the new shoots dying is Diplodia tip blight. I would recommend sending a sample to MSU Diagnostic services to see if they can identify the disease. There may be a fee for this service. 

 https://www.canr.msu.edu/pestid/

Another option is to contact your MDARD Forestry Assistance forester in Barry County, Benjamin Savoie
269-908-413

He might be able to visit your plantation to see what is going on.

If not then you can send a sample to MSU Diagnostic Services. You would want to send several branches with the symptoms. Not ones that are completely dead but ones showing the symptoms and just starting to die.