Anything to consider when staying at AirBnB in Shinjuku?

I'm planning for my 1st trip to Japan in June 2026 and currently looking at accomodations for a family of 6 ( 4 in my family + 2 from my SIL family – none of which are young children but young adults ) for a 4 night stay in Shinjuku.

I'm leaning towards staying at an AirBnB in the Shinjuku area. I wanted to stay in an area like Shinjuku where we can walk around at night while getting some late night food. I'm trying to factor in getting a large enough place where we can spend time together but also have space where we all can go to our own rooms to have some "me time". Given that we will be travelling together where it's going to hot and long tiring days, having some space is important ( mainly because I don't want to get on each other's nerves ). I would need a washer and dryer to wash clothes and also prefer a kitchen since I know that we will be warming up late night food and all.

I have a few questions that I am hoping to bounce of those that have stayed there.

1 ) For those that have stayed at an AirBnb, was there anything that you wished that you had considered when finding either an area to stay?

2 ) Was there something in the AirBnb that you should have looked for in accomodations for a short stay in Tokyo ( like having a patio area to sit outdoors at night )?

3 ) We're not going to go out and party and drink and all ( I'm getting to old for that ). But I do intend to go out late at night and get some food and see the late night life ( which I assume is somewhat safe ). I assume that Shinjuku meets those criterias, but how does it compare to other areas?

4 ) Since there is no late night trains that run after 11:30pm, how do you get around after hours?\

5 ) For accomodations where I would need 2 rooms ( One with 1 queen and 2 twin beds and another room with 1 Queen or 2 twin beds ) at a hotel, any compelling reason to stay at a hotel over an AirBnb rental?

I appreciate your comments. I have time to plan, but never having travelled to Japan, I feel that I'm considering too much when trying to figure out what to do or stay.