This will be a very long eclipse, you will have more than 5 minutes of totality in most places. The good news is that, the eclipse path will cover many bigger cities and so you have a lot of convenience choices. The bad news is that, there is not a place where the average cloud cover would be low enough and the air pollution of those bigger cities is going to be a real problem.
Therefore, we should place sight seeing as the first priority and the totality will be dessert, or an added bonus.
So far I believe that I will take my whole family with me, if that's possible. And at the same time, I believe that I will join those tours offered by traveling agency so that it will be more well organized and we will be better served.
Of course, since we still have nearly 10 more months to plan, I'll leave all options open.