Hilton HHonors - Two rooms, one Diamond, one Blue, one paid, one 50-50 award and paid - help!

I will soon have HHonors Diamond status. My Dad has only the basic HHonors card (which I think is Blue) so he gets no perks.

I want us both to stay in London for a weekend so am looking at booking 2 rooms for 2 nights. Dad wants to use his HHonors points for one of the nights and pay for the other (and earn HHonors points on that second night)as he doesn't have enough points to cover both nights. However I think it'd be better if I booked both rooms under my name as presumably we'd then get Diamond benefits for both rooms?

Would I then have to settle his bill then (therefore he wouldn't get the points for the second night) and he couldn't use his reward voucher? Or do we put both names on the reservation and the bill, his HHonors number on his room and mine on my room?

Help! This is too much for my brain and I couldn't find an answer on the search facility.

I will soon have HHonors Diamond status. My Dad has only the basic HHonors card (which I think is Blue) so he gets no perks.

I want us both to stay in London for a weekend so am looking at booking 2 rooms for 2 nights. Dad wants to use his HHonors points for one of the nights and pay for the other (and earn HHonors points on that second night)as he doesn't have enough points to cover both nights. However I think it'd be better if I booked both rooms under my name as presumably we'd then get Diamond benefits for both rooms?

Would I then have to settle his bill then (therefore he wouldn't get the points for the second night) and he couldn't use his reward voucher? Or do we put both names on the reservation and the bill, his HHonors number on his room and mine on my room?

Help! This is too much for my brain and I couldn't find an answer on the search facility.

IIRC, only the room occupied by the diamond member will receive the upgrade.
As for the certificate, you can have your dad to issue the certificate under your name, you then call the DDesk to make the reward reservation using the cert.

IIRC, only the room occupied by the diamond member will receive the upgrade.

I think it really varies by hotel, length of stay, how full the hotel is during your stay, and even perhaps who checks you in. I'm diamond and have booked 2 rooms under my name (the other had no status) several times and both received the diamond benefits - upgrades, breakfast coupons and/or lounge access, etc on all but one stay.