I think it really speaks to the psychology behind what we do and typical vacation planners.
The biggest (saddest) problem is there's probably a whole group of people who want to go on vacation but have no idea how to afford it. They're primary concern is coordinating work schedules, school schedules and saving enough money to pay for it. By the time they figure it all out they're booking too late to take advantage of some deals. This is sad - but for some reason they can't understand how CC points could alleviate a lot of this stress.
There are also people that think it's crazy to plan vacations out 12 months. My boss looks at me super weird when I start requesting time 12-18 months out. Sorry...but I like to plan ahead for these things!! Even my wife's family is frustrated when I want to lock in summer vaca dates before Thanksgiving of the prior year. It's only 6-9 months away people...let's go!!!
For these people who can't plan a vacation more than 6 months out, there's no way they can fathom earning points. They don't even know where they want to go! I try to tell them to earn flexible points that also have a cash value - ummmm hello URs?? Then when they finally figure it out, the points will be there. But again, that seems to require way too much planning. Is it really this hard to hand people free bags of cash??? I guess so!
Oh well...there loss is my gain...but I guess not really. I don't gain anything by them losing anything and they don't lose anything by me gaining anything. So uhhh their loss is their loss?? HAHA! It does frustrate me though sometimes and I just have to bite my tongue and let them spend more.