Viajero:

Thanks for the answer re: the taxes. As I said, the goal with this routing is largely to save money, so I obviously wouldn’t want to give back all/most my savings in taxes.

Here’s the routing, just fyi:

Mileage ticket: EWR-xMIA-SCL
Visit South America Pass: SCL-CJC (one of several segments I’ll be buying with that)
DONE5: CJC-xSCL-IPC-SCL//EZE-xMIA-EWR-xDFW-OGG//HNL-NRT//KIX-BKK//DPS-HKG-LHR-MRU//NBO-xLHR-xJFK-SCL
Visit South America Pass: SCL-LIM-SCL
Return leg of mileage ticket home: SCL-xDFW-EWR

Thanks very much for the feedback. Right now, I’m trying to persuade my wife that she really, really wants to fly to Buffalo from BWI so that we can see Niagara Falls, and, oh, maybe wander over to the Toronto Airport too. If not, there’s always Plan B…