I already placed an order for JR Pass at myjrpass.com. It appears the pass does come out even or slightly ahead and it has convenience at the expense of wasting 30 mins or so (may be less depending on when we get to Shinagawa) to get on the Hikari and another 17 mins additional time it takes for Hikari over Nozomi. Japan is the second part of our long 16 day trip so any added convenience will help us.
I will opt for the taxi (hopefully mini van) from Kyoto train station and Tokyo station to my hotels. I understand there are plenty of restaurants near GH Tokyo but what about near Westin Miyako? I don't think I read much about it.
Thanks you all and I will drink a round of sake on your name.