Itinerary Check: 20 - 31 Dec 2019 (Osaka, Kobe, Nara, Kyoto, Tokyo) - First time in Japan

My wife and I are traveling to Japan in 2 days for the first time. We booked this trip only a couple of weeks back and have done limited research unfortunately. I’m now getting overwhelmed and stressed about the logistics of traveling in Japan and also fearing we’ll miss out on experiences since we haven’t planned to the nth degree. Here’s our itinerary

20th December : Land in Osaka at 5pm, pick up a travel card (assuming ICOCO) from the airport and go to our AirBnB. [Haven’t booked a pocket wifi as I can’t find that lets me pick up from Kansai on a 2 day notice, only started looking today. Should I just get it when I land? Alternatively since I’m traveling in from Singapore maybe someone has knowledge of options available here that can work?] - Dotonbori at night and rest

21st December - Day trip to Kobe. Nunobiki Herb Garden, Kitano, Ikuta Shrine, Meriken Park, Dinner at Steak Aoyama (got a last minute reservation somehow!) and back to Osaka

22nd December - Exploring Osaka mainly Osaka Castle, Shitennoji and Sumiyoshi, maybe walk around Shinsekai, eat [need recommendations!], and might go to Spa World. Trying to keep this a flexible day

23 December - Day trip to Nara. Kofuku-Ji, Isuien Garden, Todaiji , may hike to Mount Wakakusa otherwise lunch nearby and walking around Nara park. Sake tasting (Harushika brewery?), might visit Higashimuki Shopping area if time permits otherwise back to Osaka.

24 December to 27 December - Check out from Osaka and check in to Kyoto AirBnB. No train tickets booked, currently thinking of simply topping up our prepaid card and using that as we go. Explore Kyoto for 3 days. Fushimi Inari, Bamboo Forrest, kinkakuji temple, Ryoanji , Kifune Shrine, Gion

27 December - Travel to Tokyo (booked Nozomi from Kyoto to Tokyo). Main activities on 27th include checking out Shibuya and Ginza , food (need recommendations).

28 December - Day trip to Hakone (depending on weather forecast, haven’t booked anything yet).

29 December - Day trip to a small/potentially snowy town or village within 2 hours of Tokyo (nothing booked, really need recommendations!)

30 December - Spend time in Tokyo (haven’t decided on what exactly we want to do but main idea is to relax and eat mostly

31 December - Early morning train back to Osaka (booked Nozomi again) to get to Shin-Osaka by 10 and to KIX by 11 for our flight back at 1pm.

Are we trying to do too much? I did the math and 14 day JR pass wasn’t worth it so I’ve booked Kyoto to Tokyo and Tokyo to Osaka and planning on just paying as I go for all other journeys. Is this a good idea? I read that the ICOCO card should work everywhere.

Really appreciate any inputs !