EWR to SJC (San Jose) prices similarly, and if you don't mind landing on a grass runway it's not hard to get to San Francisco. The nonstops used to go out with Silvers in front, I had empty seats next to me sometimes, but no more. The EWR to IAH leg has gotten tough; I nabbed my last upgrade on that leg by changing to a more promising flight at an IAH kiosk, successfully fighting the $25 charge after I got home.

For these games, the PDF timetable is your friend: Scan EWR for destinations with a nice mileage, get it done in one flight. (Yeah, yeah, the misconnect in CLE is part of the charm of a mileage run. I'm not charmed.)

I'd add $100 to your budget and make one trip out of it, to somewhere interesting. Hidden costs for two boring trips will make this a push, anyways.

If CO raised its top elite level to 100K, many of us will be going through this exercise, to top off and enjoy a few short trips here and there. Doesn't have to be MR aesthetics to the trip, it could be grabbing a sale to somewhere far and amusing, on a nonstop that won't lead to trouble.