The fare diff. from S to W should be relatively small (<$100) + well worth the trip upfront. As a 1K you should have no problem getting the upgrade. I'm not sure about your companion (if no status), but certainly someone on this board will know!

If you have many e-SWU and not that many miles since a lot of your travel is on short haul (but lots of segments), you might think about checking out the coupon connection: several people are swapping e-SWU for miles/awards. BTW, I found the CC FAQ to be very useful.

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