Thanks for the responses! I think it will be 2/3 me and my wife and 1/3 our daughter.

So I spend about $125,000 on my card in 2023, 25% food and drink, 20% "shopping" and 15% travel.

I use the Chase points diligently, and always book through their travel portal. Would definitely use the United Club at O'hare and would probably be happy to check a bag.

I tend to use Hiltons, but I don't stay in hotels that often (I use Air BNB).

I have actually never used the transfer points to miles feature, because I have hard time figuring out if it is worth it.

Thanks so much, this is incredibly helpful!!!!