Hilton HHonors - Gifting award stay to family member

Just wondering what is the best way to give my brother and his new bride (who have no status with hilton) a free night at a local Hilton using my HH points. Do I...

1. Book the award reservation under my name, hoping the hotel is generous to me as a diamond member for a nice upgrade. Obviously I would need to go to the hotel and check them in, or do so in advance and have an envelope waiting for them with the keys, maybe put $100 on the account for a nice dinner.

2. Call the HHonors desk and book the award reservation under their name. Let them deal with checkin, give them a $100 bill to do as they please.

Or are there other options to consider? Would appreciate any advice on what is the best way to do this. Thanks!

The traditional way is for you to book the award in their name, they check in, etc.

However, if you are local and want to check them in then you would likely get the preferred benefits.

Are you going to pay for the room?

I did this for my stepson and his new bride at a Marriot property. Went and checked them in, put up my credit card, they got hubbys PLT status bennies.