Booking Hilton Rooms for Family with Points vs. Cash—Questions

[FrenchLondoner]

Hi all, I’d appreciate some advice on booking a Hilton stay in central London for my visiting family (a couple and their two teens, ages 17 and 19). My flat’s too small to host them, so I want to treat them to a hotel stay. My partner and I are both Diamond members, and I’ve found a Hilton with reasonable rates. However, I’m trying to navigate a few concerns and would love your input—no judgment, please, as I might be overthinking this!

Here’s the situation and my questions:
– My sister’s family earns less than me, and I don’t want them to know the cost of the hotel (it might make them uncomfortable), but I still want them to enjoy a nice stay. I’m considering buying Hilton points to book two rooms and avoid any visible cash price.

– If I book two rooms with points for them (two adults, two teens), I assume the rooms can’t be in my name since I won’t be staying there—does that mean no Diamond benefits like free breakfast?

– Alternatively, could I book three rooms with points, adding my partner and myself to two of the bookings (without actually sleeping there) to secure Diamond benefits (e.g., breakfast for four)? We’d be present for check-in and check-out but stay at our flat overnight—does this work, or is it pushing the rules?

– I’ve also noticed a cash rate that offers better value than points. If I book two rooms with cash, could I contact the hotel afterward and ask them not to disclose the rate to my family?

– Another option: book three rooms at the cash rate—two under my name, one under my partner’s—to maximise Diamond benefits across at least two rooms. Would this make sense?

– Lastly, if I book two rooms under my Diamond account, would benefits (free breakfast, upgrades) apply to both rooms or just one?

Any insights or suggestions would be great—I promise I’m not as complicated as this sounds! Thanks in advance.