For example, the JR Kyushu Blossom Shinjuku is in your price range. It lacks the faded prestige of the Keio, but it opened recently (2014) and is arguably a little better located (although still a little sterile for my taste). In terms of access to Disney, it's close to Shinjuku Bus Terminal where you can get a bus directly to Disney without having to deal with awkward connections:
https://www.booking.com/Share-vj47LG

The other hotels that you mentioned - Keio, Cerulean, Daiichi - suggest that you're looking for a hotel with a certain cachet, even though it may be dated. I don't value that, but you might. Ultimately you are the best judge of what works for you .... which is why it's really pointless to ask random strangers to do the searching for you. Any of them would be okay places to stay, I guess. So perhaps you should just go with your gut.

is airport duty free for sony headphones the same as tax free in tokyo? But Haneda did not have any shops with electronics as they were closed due to COVID.
Or does anyone know if there is a shop at Haneda that sells sony noise cancelling headphones?

See below.

“…There is a free online website called Hyperdia, a rail planning application that is easy to use…”

Hyperdia no longer provides detailed schedules, only “ranges”. Essentially useless.

The very next day. Things work in Japan. There are no slackers there like you’ll find in Kalamazoo or Albuquerque.

This is a response to a post from 5 years ago and unnecessarily aggressive.

Unrelated question for locals:

Do you usually need tickets for things like the Snow Festival? It's a bit hard to tell from the official website if it's just open entry or ticketed.

You didn't used to need tickets -- and I don't think that has changed post COVID. The main site being outdoors is (was) open 24/7 -- but they do turn off the lights before midnight IIRC.

Regardless -- I'd worry more about 1) tickets to get t the region, and 2) accommodations....

I have our accommodations booked (JR Tower Nikko Sapporo) and we'll be taking the train up. I do need to book our return flight to HND though. We're going to utilize the JAL Explorer Pass to fly back, do those tickets sell out?

Yes, JAL Explorer Pass is capacity controlled. I have seen that on a holiday (Japanese holiday...) JAL Explorer Pass was available only on the first flight of the day (i.e. 7 a.m. departure) and was not available on the remaining flights of the day.

I was going to wait but I'll just book them now. Thanks!

Didn't get to do a Ryokan stay but will definitely the next time. Your tip on the extra bedding will come in clutch! :) Looking forward to it on my next trip out to Japan! I've did find some restaurants uncomfortable when they do the sitting on tatami mats with a low table for eating.

Thank you for these insight about the blackcat service. I wasn't aware that people didn't usually take luggage on the Shinkansen when planning our trip. Is this service limited to hotels only? I was originally planning to stay in some airbnbs vs hotels at various points during the trip.

no. It's available everywhere include convenience stores.

I am visiting Japan late Mar-mid Apr for 2 weeks+, mainly Tokyo to Kyoto then back to Tokyo. Will appreciate some feedback on (1) should I buy JR pass in advance, or upon arrival in Tokyo?
(2) about Shinkansen - do I need to reserve the train/time for my family just a few days or much earlier?
(3) The night before we will stay at Andaz Tokyo, then the next morning to Haneda Airport. Return flight will be around 11a, so I feel we should have enough time. Looks with luggage best option is taxi?
(4) I am tempted to reserve some restaurants. A friend used Tablelog but it only worked within Japan. My current stay plan is mainly a mix of Park Hyatt, Conrad, and Mitsui. Any other app may work well enough in US? Shall I call the hotel concierge for some help?

(1) should I buy JR pass in advance, or upon arrival in Tokyo?
JR is doing limited time thing where JR Pass can be purchased at selected JR ticket office in Japan, but this is until March 31, 2023 and JR has not announced that they will extend this beyond March 31. But buying JR Pass before arrival will eliminate one thing you have to deal with once you arrived in Japan.
Also, if all you do is a round trip of Tokyo and Kyoto on JR, then JR Pass will not save you money. It will be cheaper to buy round trip Tokyo - Kyoto Shinkansen ticket.

(2) about Shinkansen - do I need to reserve the train/time for my family just a few days or much earlier?
You do not have to reserve Shinkansen tickets in advance, but recommended. It is busy business route and sometime trains do get sold out. Busiest time for Shinkansen is Friday late afternoon and evening, also holidays. Also, last week of March and first week of April is school holiday in Japan, kids are out of school. Also, it is cherry blossom season with a lot of non-Japanese visiting Japan. Shinkansen can get little busier during that time. Buying tickets in advance will also endure that your group/family will be able to sit together.

(3) The night before we will stay at Andaz Tokyo, then the next morning to Haneda Airport. Return flight will be around 11a, so I feel we should have enough time. Looks with luggage best option is taxi?
Yes, I say taxi is a best option.

(4) I am tempted to reserve some restaurants. A friend used Tablelog but it only worked within Japan. My current stay plan is mainly a mix of Park Hyatt, Conrad, and Mitsui. Any other app may work well enough in US? Shall I call the hotel concierge for some help?
If you are dead set to have a meal at the specific restaurant, then reaching out the hotel will be one of the best ways to get a reservation at the place. I am not the type I have to have a meal at the specific restaurant. Tokyo and Kyoto have a lot of restaurants. Pretty much all I do is in late afternoon I call restaurants or ask a hotel concierge for recommendation and find a restaurant for that evening. This always worked for me. But if you are set on the specific restaurant, then reach out the hotel before arrival at Japan.