This is something I have much interest in doing, likely a DONE5.

Would someone mind answering two questions?

With regards to the 16 segments, say my goal was to have a stopover in Washington, DC and a stopover in Appleton, WI. The only available OW route is WAS-ORD-ATW via AA. Does this count as one segment since I am only connecting in ORD? Or is it two segments? EDIT - or maybe this counts as a 'free' flight segment?

Is there a tool to determine what is the best FF flyer program to credit the flights? I figure if I am going to do this, I may as well benefit with OW status with some airline.

(This is a great thread. I appreciate the time and effort it took to put this together!)