Let's say someone has an itch, maybe some gift cards, and wants to pick up many segments, lounge visits and maybe sip on glasses of $13btl of wine at fl30.

Is there a way, with EF, Matrix, or perhaps cowtool, to search for (and book online) what sane people would consider the worst routing, given the fare rules? (Or, let's not be crazy here): the worst routing with some limitations like airports with open lounges.

Or is this mandraulic to plan, and requires talking to a human to book? And would such a human give one grief?