This is my first OWE and still a work in progress.

Proposed itinerary is

yyz-jfk-lax-den-bos-dfw-lgw-ams-lhr-dxb-lhr-hkg-nrt-hkg-kul-hkg-jfk-bos -- 40079 mi

(just transiting at jfk [both times], den, dfw; obeying the max of one stopover at each of lhr and hkg.)

Questions --

Better use of the NA segments? I do have business in each of YYZ, JFK [first transit], LAX, and DEN; the DFW transit en route to LGW is for a quick visit to the nearby Six Flags (!!). Any way to go to the Caribbean here? If I could save a Caribbean round-trip for the end of the itinerary, I might well do so. But it seems like I can't do a Caribbean r/t because of the rule (at lines 160-162 of OWE rules) that only one international departure and arrival are permitted from/to the country of origin. Certainly I'm making poor use of the proposed final segment (JFK-BOS) which is a $25 bus ride or $80 shuttle fare (thanks to corp discount), a segment that I perhaps ought to try to put to better use elsewhere.

Better use of the Europe segments? I actually have some business to do in DXB, so it's not a pure mileage run. And also business in AMS. But AMS is cheap and easy enough to get to that I could buy a separate r/t ticket for LHR-AMS-LHR and use my OWE segments to go elsewhere. Advice?

Better use of the Asia segments? I have business in KUL, but none in NRT. Chose NRT solely because I thought it would be nice to experience CX's special service in F on this route (assuming I end up booking in F). But maybe there's somewhere that's 1) further from HKG, and/or 2) a better tourist destination? I've been to Tokyo repeatedly, and love it, but probably wouldn't stay for long on this trip; another spot in east Asia might be better for me. Hmm.

Opportunity to add another continent? Fewmiles's RTW fares show 3-continent F OWE originating in Canada at 10500CAD, while 4-continent is only 700CAD more, 11200CAD. I guess I could add a pure mileage run to and from South America. In AA Flagship Suite F, it's perfectly pleasant to do this, and that's a lot of miles (including a lot of Q-miles) for 700CAD plus taxes.