2 rooms - 2 memberships or 1?

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Planning a couple of Hilton stays where we will require 2 rooms (20 & 16 yo travelling with us). Are we better off booking both under 1 membership or 2 separate memberships to increase chance of upgrades, point values etc? We are both gold.
 
I booked 2 rooms in my name last weekend at HSW and both were upgraded to 2 room suites.
 
I've booked two rooms under one account previously and one was upgraded, but to be fair, the other was a double double, which is what I wanted for the kids over an upgrade and I think I did advise them of that (can't be sure now though). All privileges were extended to both rooms (including lounge access and breakfast for 6 :shock:) Can't whine about that at all.
 
Hilton KL would only extend Gold benefits to 1 of 2 rooms I booked last year.
 
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As a Diamond if booking 2 rooms for 4 people should I expect the benefits to be honoured for both rooms? Not sure if this is mentioned anywhere in the terms and conditions or if it is up to individual hotels.

It gets a little more complex as what I really want to do is book 1 room for 1 night and another for 4 nights.

Myself - Night 1
Friend - Night 1, 2, 3, 4

I want to make the booking in such a way that at least I get Diamond benefits for 1 night and my friend gets my Diamond benefits for 3 nights.
 
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