Most of the info you're looking for is on the Hilton website. Perhaps you could study that then post specific questions if you have any.

Airlines:
http://www.hilton.com/en/hhonors/rew...change_1.jhtml

MR:
http://www.hilton.com/en/hhonors/rew...change_3.jhtml

The best way to get quick easy free or almost free points is MyPoints. See the S.P.A.M. forum for the current status of Tupperware, Amtrak, Zappos, surveys, and other offers, as well www.MyPoints.com.

My wife and I have posted over 16,000 HH points in the past few weeks via MyPoints offers and redemption. No guarantees, though, as they seem to be getting smart and closing accounts that take maximum advantage.

BTW, you and your friend may be able to pull of a mutual fund. Non-spouse MF's have been reported with mixed success -- some have gotten it, and others have not.