Hyatt guy here, questions about booking Conrad Osaka and what status can do to help

Hey Guys. Hope it's not too rude to ask a few questions as I know very little about Hilton. Any advice would be awesome.

I have 7 people, 5 adults and 2 kids (7 and 9) all needing to stay 2 nights in Osaka in the summer 2024. 4 of us can all stay in 2 beds (my wife and our 2 kiddos). 2 of the other 3 can stay in the same bed too. Hyatt has left Osaka so that's why I am here.

Looking around I really like the location of the Conrad, and if I am going to dip my toe in to the water of Hilton, I might as well do it with class!

Mt questions:

  1. I am looking to status match my Globalist status with Hyatt (if available next summer) to receive Diamond status for 90 days. If I do this, what are the odds of an upgraded room? With Hyatt I am always supposed to be upgraded if there is a better room available and sometimes I need to remind them for the upgrade (after checking online for availability). Is this the same with Hilton?
  2. Why I ask about the upgrade is the 95,000 point a night room I am looking to book 2 of is the Twin Deluxe Room. It appears from the pictures that there are no windows in this room. Is that possible? I've never stayed in a hotel room without windows, especially a nice hotel.
  3. We have 4 of us for 1 double room but when I search 2 adults and 2 children nothing comes up. When I search 3 people total, I can see the available rooms. Then I read this saying to book 2 adults only if we don't need any additional beds. Does this sound legit? The room says 3 person max on hilton.com.
  4. I will be transferring points from Amex. They have a bonus for 30% more points when transferring to Hilton, so 1:2.6, instead of 1:2. So for 2 rooms at 95k for 2 nights it is 380,000 Hilton points, or about 146,154 Amex points with the bonus. That sound right?
  5. Any advice on what I am trying to do? Is there a better way to do this? Any ideas are very welcome!

Thank you in advance!!!