Thank you so much for addressing my concerns. Really appreciated it!

Looks like our trip is almost mirroring yours in terms of when we'll be there and where we're visiting/staying (although we're going through to Osaka after Kyoto, then back to Tokyo).

I've been trying to decide between pocket wifi and e-sim, seems pocket wifi is much easier to get connected but at the same time I'm hesitant to wait in line for the pocket wi-fi after arriving in Haneda, we just want to get into the immigration lines quickly. Have you decided what you plan on using for cell phone data? E-sim will at least let me venture off on my own from my wife if I have to and not worry about one of us no longer having pocket wifi, I may just be intimidated of its setup. Wondering if you had a good strategy for that.

Just chiming in since this might help
1) I used Ubigi for data - esim purchase -just don't activate too soon. It was MUCH cheaper than any other way of purchasing data for me and worked fine. It was easy
2) Don't know if this is relevant but - all over Japan there is a transport system that will pick up your bag and deliver it to your next hotel or the airport for very reasonable rate. One day before for delivery within Japan (at least for close points) or two days if it's for airport delivery. (You can also have your bag sent from the airport when you land if it's heavy/inconvenient)

Thanks for your helpful input estnet! I went ahead and installed the Ubigi esim and you're right it's actually easy. I'll purchase and activate the plan either the day of our flight or when we get there (since I'm going for the 10gb/30day plan, and we're in Japan for 17 days, should be fine buying and activating before we take off and would be nice to have it all ready to go when we land).
Question, did you turn off your primary SIM when you turn on and use the Ubigi SIM? (If I have to call back home to the US, I was going to use wi-fi calling to avoid paying, and iMessage on iPhone will work with either wifi or the Ubigi data). I can just let people know they have to iMessage me to reach me, and I can call back on wifi.

Thanks also for your suggestions on luggage delivery, we're also looking at that as an option. Appreciate all your help.

We went with a pocket WiFi from Ninja. It was brainlessly easy to use after a 5 minute setup but we didn't realize there was a 3 GB daily limit before throttling with our plan, which we actually hit a few times without realizing. We also had Verizon's international plan as a back up for when we split up. There's other providers (Japan Wireless is one) that has truly unlimited data for pretty cheap rates as well. Also, you can pick up your wifi AFTER immigration at HND for Ninja Wifi and I think Japan Wireless delivers to your hotel before you even get there.

My wife and I used e-sims and they worked very well for us. You will need to verify that your phone has e-sim capabilities. My son's phone did not and we had to get a physical data sim card for him.

For experience purposes (not at all meant to be an endorsement) our trip included Osaka, Kyoto, Nara, Chino, Suwa, and Tokyo and the Ubigi e-sim worked very well for us. We got the 10gB over 30 day one off e-sim and it was more than enough for our 10 days there.

There will also be plenty of places that you can connect to the wi-fi and not need the cell data which saves the usage.

It may be important to look at the different e-sims to make sure you do not get one that throttles you connection speed if you exceed too much data in a day or week.

Just my experience...

Thank you all for your help! (@estnet, I actually responded to your help earlier, not sure why my reply wasn't posted).
I've just installed the Ubigi esim on my iPhone (13) and it actually was very easy, so I think we'll be going this route and activating the 10gb / 30 day plan while waiting before takeoff (since we'll be in Japan for 17 days that should be fine activating a day early, and when we land in Haneda it'll be nice not having to worry about it). Pocket wi-fi looks very easy too, but e-sims for our use is probably better.

Another question I had regarding using esim was if you turned off the primary e-sim (in my case AT&T). I plan on using wi-fi calling for calling back home, and texting will be free to text other iPhone users (both back home and my wife with me in case we go off on our own for a bit). I want to avoid any unexpected charges in case someone were to call me not knowing I'm in Japan, (or maybe this doesn't incur a charge if I don't answer?).

Thanks again for all your input, really looking forward to my first time in Japan.

I don't use iphone but I think this is true for all phones. You can only use 1 sim at a time so when you select the ubigi sim your att is not active. I don't know what happens if you switch back to ATT to use wifi to call to the US and someone calls you while it is active. I use google voice to call over wifi and never activate my US sim. I was also in Japan for less than 30 days, but the $8 was so much cheaper than the shorter time plans I was glad I made that choice.
I don't know how att charges if you don't answer and your att sim is active.
Have a great trip. You might want to look into whatsapp - works only on data, you can make calls and text -so if you and your wife both have data you can connect anywhere with no charge.

Isn't Osaka renowned for street food?

I would say Fukuoka with the Yatai. I honestly don't remember seeing much street food in the few times I've been to Osaka, then again I didn't really look very hard for it.

iPhones and some androids (OnePlus dual sim models) allow for active-active sims. on iPhone 13 and above you can have two active eSims and set which sim will make phone calls and which will be used for data. On my OnePlus, I can actually drop down the slider and swich which one's internet I will use, at any given time, but they both remain active and you can set it to use both for internet, or switch to the other when one goes down.

https://support.apple.com/en-us/HT20...active%20eSIMs.

I watched this program https://www.imdb.com/title/tt11438508/

James May of Top Gear fame, and a national treasure in England.

Would give it a watch if you can find a stream.

James May gets taken to Honke Ootako in Dotonbori for takoyaki. A small restaurant where you can order to take away or eat inside… is that street food? Everyone seems to have their own ideas and definitions. Is a fish and chip shop where you can eat inside “street food”? I really have no idea where common ground is on the term.

The place James May was taken for Kobe Beef was Wanomiya. His portion cost about 10,000¥
1 Chome-5-2 Dotonbori, Chuo Ward, Osaka, 542-0071
Just cannot find a way to agree that this is “street food”.

And that was the conclusion of the “street food” tour in Osaka.

Very different to wandering along a street in central Bangkok, particularly in the company of MrLapLap.

I think my definition of street food in Japan includes food vendors (with human staff) where you can eat the food outdoors in public and don't get the stink eye from other pedestrians. Come to think of it, I don't think I'm coordinated enough to eat scalding takoyaki while walking. Other than perhaps yatai, office bento/food trucks, and festivals, I feel like street food in Japan trends towards snacks rather than full meals. I usually keep my eyes open for street facing stalls/windows around temples and in tourist areas Japan Travel: Japanese Treats at Temples and Shrines - Pechluck's Food Adventures along with the occasional yam or chestnut vendor. I can't speak for the Harajuku style crepe but that style of crepe was popular in my local Japantown, I just haven't seen one sold in young women focused shopping areas which looked appetizing.

There are places I'd sort of categorize as a food market or Hawker center like Hirome Market in Kochi, Karato Market in Shimonoseki, and Aomori Nokkedon.

Yours and my definitions seem to be in alignment at least.
Another candidate that will actually tempt the LapClan are stalls/open counters that offer freshly cooked seafood at seaside locations. Mobile molten takoyaki is tricky enough, but my biggest walk and talk and chew challenge was when I was presented with a sizzling sazae (turban shell) by MrLapLap’s dad in the Matsushima area. Harrowing!
My kid’s all time favourite “street snack” was discovered not so far away at one of those places with a full span of weird and wonderful ice cream flavours, but maritime themed, because, by the sea. She decided on jellyfish flavour and proclaimed it the best ice cream she’s ever had. Still does. It actually was very nice.