Interesting turn of the story... with a route that distant, you might consider piecing together multi-segment trips between OAK and ORD. That might fast track you to elite status faster. i.e. don't fly non-stop. Book each direction with an innocuous stopovers.. e.g. Minneapolis or Denver or some-such... One round trip = 4 segments.

*only during non-winter months*!! Every extra stopover in the midwest during winter is a high risk of cancellations and delays and headaches.



Either way you strive for elite status, attain it quickly. Then think about leveraging that for a status challenge for the remainder of the year on another airline.

Hehe, I wish I had your "problems".. I was a long-term-travel consultant for a number of years... before I knew anything about the value of points and miles, etc. Now I live where I work (and wouldn't trade it for airport life for anything), so the compensated opportunities are scarce (... I'm self employed, so getting reimbursed for travel is just taking money out of my left pocket, instead of my right)...

Anyway, again, good on ya' for looking and thinking about the bigger picture of your job perks.