I know this question is not easy but appreciate any advice.

As a Diamond if booking 2 rooms for 4 people should I expect the benefits to be honoured for both rooms? There appear to be reports of this happening although 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 4
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 the other 3 nights.

How would I make such a booking? Make a booking in my name for 3 nights with a guest? And then make another booking for 1 night in my name for 2 rooms?

It all gets a little confusing trying to be too clever....