So hard as to be almost impossible probably given your routing above. Please post your success if so but it just seems impossible.

The only thing I could see saving it is an **extremely** flexible travel schedule, where you could book the segments on almost any day as long as they are in the right order, and maybe try to change some later.

But given the 330 day issues, you'd have to probably find all those segments in a row, in a short period of time (like a 1-2 month trip) and then successively try to change the later flights as you go.

And even then you run into the issue of the ticket being valid for a year, so you'd have to issue right before leaving, when most seats are long gone.

If I was facing this situation I'd find the money for a LONE/DONE and rack the miles up for some status and great point to point trips in the future, like US-SA or US-EU and back for you and a friend in a premium class.