My philosophy is similar to this. pretty much all my travel is for leisure. Like a dollar, the value of a point is always higher today than tomorrow. I will pay for cheaper flights to reposition myself to cities where I can get business/first class reward flights to my final destination. I'll usually arrive in the "repositioning" city a day or two beforehand, to preclude any unforeseen delays that might prevent me from boarding my reward flight. It also give me a mini-vacation in that city, and ensures I'm well rested so I can enjoy all the perks of the premium flight.