2 different booking at same place same date
 

If I have already book a room and make another one to at the same place and dates, do I get the benefit (points and breakfast) on the 2nd booking?

No.

Well actually you do get the points although you will either have to combine the folios before checking out or asking them to do so after the fact.

As far as breakfasts go do you really want to eat two of them? It is a benefit for you and a guest staying in your room. But seriously sometimes a hotel will give you breakfast coupons for a second room even though you are not entitled to them and sometimes they don't.

Upgrades work the same way, they may or may not upgrade a second room.

That is the upgrade rule at Hilton in general for every room, even for the first room.

Ok. I have additional people coming on the trip thats why need to book another room, was checking because I have booked my room without breakfast(since will be getting the 2 free one) so wondering if I should booked bed and breakfast for the second booking or just bed.

But I guess the conclusion is the 2nd booking will not getting the gold perks so I should just book them with breakfast. Thanks