Trip planning questions

I am planning to land in Osaka and fly out from Tokyo. I am trying to squeeze in an itinerary for 7 day JR Pass although, I am also checking and it seems like it might be about the same to buy single tickets.

Day 1 land in Osaka @ 2200 - I booked a hotel at Park Osaka ( It seems a bit far on the map, can you tell me what is the best way to go from the airport, especially at night?)

Day 2 Osaka full day

Day 3 Osaka to Nara and back to Osaka at night

Day 4 Osaka to Kobe and back to Osaka at night

Day 5 Osaka to Kyoto- stay in Kyoto

Day 6 Kyoto full day

Day 7 Kyoto to Nagoya

Day 7 Nagoya to Kiso Valley - stay in Tsumago for a night

Day 8 Tsumago to Yokohama ( Do I have to go back from Tsumago to Nagoya , in order to head to Yokohama?)- is this very far?

Day 9 Yokohama to Tokyo

Day 10-13 Stay in Tokyo

Is it best to activate JR Pass on Day 5? ( Is buying single ticket to Nara or Kobe quite cheap? or should i purchase a Kansai Thru pass?

Or am I better off buying single tickets; if so, how does my luggage work? Do I still have to reserve seats?

Lastly, since I am covering a few areas in Japan- I've read about visitors renting a pocket wifi, is this necessary and which is the best option to cover major japan cities?

Thanks so much

I would buy a Kansai Thru Pass. And use it for Nara, Himeji, and Kobe.

A JR Pass wouldnt be that worthwhile unless you do a side trip to places like Amanohashidate or Kanazawa.

I would recommend spending more time in Kyoto over Osaka. But that is just my prefence. (Tokyo is more interesting as a city. Osaka is special due to the Sakura viewing and the night life about Domtombori)

Would you recommend buying a JR pass or single tickets?