I routinely do this for three reasons... First, to gain # of stays when trying to advance status (I did this to get to diamond faster). Second, to gain the additional 1,000 points upon check in. Third, to maximize the free night promotions. I have not done the side by side hotel check in/out, as my most popular destinations do not have this luxury, but would if I could. I do, however, check in and out of hotels that are nearby. Because I am after the points, I only do this if I can get competitive rates at Hilton and Doubletree in the same city. Occasionally, I'll stay at a Waldorf and try to look for a Hilton Vacation Club (2,000 points on check-in). This strategy allowed me 3 certificates in Q1 and with some good planning, should get 4-5 in Q2. It seems kind of silly to ge throught the check in/out process, but ultimately worth the effort with the quarterly promotion payout.