It looks like my plan is to take my luggage from NRT to my Shinagawa hotel myself. I hear the NEX has ample room.

I will forward my luggage to Osaka (Tennoji) the night before I check-out in Shinagawa.

I hear that Japan hotels aren't very good about early check-in so....
I'll eat breakfast early
Check-out in Shinagawa
Around 8am, take the bullet to Nagoya and watch about 2 hours of sumo and visit Nagoya Castle.
Bullet to Kyoto, and visit the Fushimi Inari Shrine for about 2 or so hours.
MAYBE bullet to Kobe and take the Nunobiki Ropeway and maybe try some beef.
Bullet to Shin-Osaka then train to Tennoji

By that time, it should be after check-in time easily and hopefully, the luggage will already be there. I will call the hotel the day prior to give them a heads up.