You'd be surprised how many people will think you're not crazy. They understand the concept of "buy one, get one free."
I'm trying to set up a $650 ORD-BRU-BCN-BRU-ORD the weekend before Thanksgiving, to visit a former student and her family. 9400 status miles on my quest for Executive Platinum, 33,600 total miles after various bonuses.
I was hesitant to explain this to my parents, but when I did I was shocked. My mom, one of the most risk-adverse people I know, thought it was a wonderful idea!! She insisted that I should go someplace every other weekend for the rest of the year as long as I could keep it under 2 cents/mile.