How many stays will I get in following situation? I have booked consecutive 3 nights in HGI Times Square, 2 nights in Hilton Times Square, and again 2 nights in HGI Times Square. But aside that for the same time 7 nights in HGI Times Square for two friends, not family members. I will be paying all the stays.
To ensure myself three stays, should we arrange a different payer for the 7 nights in HGI?
That would be a tough call. Sometimes where there is a conflict in bookings it seems they choose the one to give the lesser benefits. I doubt they will look to all four of your stays but instead just the two that conflict, probably after check out on day eight. My guess would be the three-night stay as they would likely have fewer points. You'll still get your three stays, but those points from the seven-night stay would be lost until claimed.
If I was doing the same thing, I would look to move the seven night stay to someone else, hopefully with an HH account already, or a new account just to capture the points from the stay. Also, is there a reason the other party can't/won't move with you? Yes, it's more of a hassle, but at least you can gather the points for both rooms. And, if you put them on a Gold promo, they'd only be one stay away from Gold status (bonus points).