You can't feel pity for your friends who are ignorant of how the system works. It's like anything else - finance, shopping, real estate, etc. If you want to get the good deals, you have to do a little homework.

In your example, a Diners Club or AmEx would fit the bill nicely - transfer over 5k miles and you are there!

What I find appalling are all of the poorly-capitalized "quasi"-miles/points programs that can and do close up shop all the time, stranding everyone's points.