It is an interesting collection of cities.
It will likely still be winter when you get to the Northeast. It might even be winter weather at the places you are visiting in Virginia and the mid-Atlantic. You might be arriving at Mackinac before the Grand Hotel usually opens for the season, but the ice should be gone and the ferries running out to the island. I last stayed at the Grand Hotel in early June 2013, it had just opened for the season.
I've planned several road trips in this much detail, have found that I'm usually off schedule by the third day, can be more than a day off in less than a week, but that's because when I find something interesting that I did not plan, I stop to do it.
Some of your driving days are well over 300 miles, a few more than 400. I find those exhausting, and certainly would not want to be doing two or more back to back.
Whatever the criteria for livability, why visit cities where the climate is not what you might want to endure? For what it is worth, this summer and earlier this fall my sister in law and husband celebrated her retirement with a 8000 mile trip visiting cities on a list of places ideal for retirement, didn't find any place compelling them to move from where they are now, which is Detroit. Across the Midwest, down the West Coast, back through the Southwest into the South (which your list seems to be avoiding, but might be the least expensive places to live and have the least expensive labor, and room for market growth).