Thanks for the replies.
I am trying the fix for the SWP segments. I am not able to find the per-darwin-syd or per-cns-syd on cathay pacific timetable. Also I thinkg the routes you specified are crossing the 2 segment limit for the continent of origin.
As for NA segments I live in MKE and plan on taking a break after the SWP, Asia trip before visiting ANC and later SJU. I thought that there are seasonal flights ORD-ANC in summer.
As for the Canadian AA membership, I can easily change my AA account to a canadian address, but wondering if they will have the same benefits as US members especially VIPOWs etc.
Thanks for the replies.