The first day, leave early and get to Southern VA.
I think that once you get past the NJ/PA border you'll have a lot less
chance for some sort of trouble.
Don't worry, I think I will make that a 10+ hour day and do the rest at a leisurely pace and enjoy the drive. I think I might be taking something similar to the second route that you mentioned because I am caravan-ing with a buddy who is also going to pilot training at Columbus AFB in MS, so we have to make a pit stop there along the way. And I will be headed to Sheppard AFB up in Wichita Falls... it is basically Oklahoma and in the middle of nowhere unfortunately. Nothing to do but shoot guns all day!