I'm not experienced enough to help you much. My gut reaction on a group of five is that is going to be exceptionally difficult and to get a pro, many people offer this service. If you want to do it yourself, then you have a lot of reading to do. I can help you search for it, but that's about all I could do for you. I'll post some threads that may help.

http://www.flyertalk.com/forum/miles...ple-miles.html

http://www.flyertalk.com/forum/miles...el-awards.html