Grant Grant's original plan to attack Richmond via New Berne.

"In the end it has to be considered that Grant was not an island unto himself, he factored in advice and reports from staff, corp commanders, politicians, friends, spies and others when developing military actions. His actions, like any commanding officer, were subject to review and he was subject to dismissal if any of his actions proved untenable to the War Dept. & Washington."

...Because of this I'm unsure if 'his first visit to Washington' , after which he 'never dreamed of undertaking or advising the operations above', was what influenced him or whether it was a combination of factors including his own assessment.

Yes, the political situation and the priorities of Grant's superiors (including the Commander in Chief) had to have entered into decision-making at least as much as the purely military (possible) advantages of the New Bern proposal.

Roy B.
 
And I think THAT'S the key to this decision. Lee's almost magical stature in this war, in the minds of his contemporaries (except possibly Grant, part of why Grant was the right person to beat him!)

Militarily the southern attack route was very sound. But the potential for Lee to do the unexpected - the CONCERN his reputation created over that - was an overwhelming factor that we know can never fully appreciate.

I think - my opinion only - that THAT concern was key to the overland decision. It was a psychological factor that we armchair generals cannot properly measure, when we count miles per wagon, attack odds, etc etc.
I found this in Ulysses memoirs which might be relevant to what you are suggesting here:

"One of the most anxious periods of my experience during the rebellion was the last few weeks before Petersburg. I felt that the situation of the Confederate army was such that they would try to make an escape at the earliest practicable moment, and I was afraid, every morning, that I would awake from my sleep to hear that Lee had gone, and that nothing was left but a picket line. He had his railroad by way of Danville south, and I was afraid that he was running off his men and all stores and ordnance except such as it would be necessary to carry with him for his immediate defence. I knew he could move much more lightly and rapidly than I, and that, if he got the start, he would leave me behind so that we would have the same army to fight again farther south and the war might be prolonged another year.

I was led to this fear by the fact that I could not see how it was possible for the Confederates to hold out much longer where they were. There is no doubt that Richmond would have been evacuated much sooner than it was, if it had not been that it was the capital of the so-called Confederacy, and the fact of evacuating the capital would, of course, have had a very demoralizing effect upon the Confederate army. When it was evacuated (as we shall see further on) the Confederacy at once began to crumble and fade away. Then, too, desertions were taking place, not only among those who were with General Lee in the neighborhood of their capital, but throughout the whole Confederacy. I remember that in a conversation with me on one occasion long prior to this, General Butler remarked that the Confederates would find great difficulty in getting more men for their army; possibly adding, though I am not certain to this, "unless they should arm the slave.""

We see Grant mulling over the possible options and moves Lee could make, fearing the war could be prolonged in the circumstances. And the possibility of slaves being armed had already been suggested. Plans had to be malleable to a certain extent in the knowledge that the enemy could be unpredictable. Moves and countermoves as they say.
 
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