Doyle,
I'm not sure I would say that most historians would say that the war was almost over by August 1864. But, I haven't really looked into the matter. Do you have some examples of historians saying this?
I am not surprised that Douglass would have been hesitant about a Union victory at that point. The Confederacy still had a lot of fight left. And, as you mention, the presidential election in 1864 was anything but assured for Lincoln. Democrats under the very popular George McClellan were making a strong showing, and that party was not particularly concerned with black rights or interests---or even emancipation. Douglass surely would have recognized that.
I completely agree that Lincoln was being sincere with his compliments of the USCT. I believe that he did recognize that they played an essential part in the war effort.