Hi -

I'm having a bit of trouble unwinding the best way to accomplish what I want so I was wondering if I laid out my objectives if anyone could help.

Criteria:

- I fly 5 or so international round trips and 15 or so domestic
- I want my probability of flying first to be in the 90%+ category. Willing to pay what it takes but want to mitigate cost with the tools I have.
- I have delta platinum medallion and 1 million miles in my delta sky miles.
- I always travel with a companion, assume she has no status or silver status with delta. I can probably cajole a higher status out of hers but not platinum like me.
- I have Amex platinum.
- I have delta reserve amex
- I always want her to fly up front with me.
- I am flexible on my dates and times to fly

So I've got a bunch of options.. I can do Amex free companion which saves a bunch and ensures first and is refundable, but is often still pricey.

I can book and try to get upgraded but her status holds me back, no?

One idea I had is book one set of flights full fare first w companion, then another set full fare coach and if upgrade succeeds get the first tickets refunded. If upgrade fails, eat the cost of the coach tickets or get them refunded or switch them to a placeholder trip in the future.

Maybe there is a huge hole in my plan, maybe there's a simpler or better way?

Given the criteria laid out, how would you approach?

Thanks!