well thanks all for your great advice! i decided i was not man enough to go with tvl4free's TPE run, brilliant as it is. special thanks to keithguy as well - his advice helped to find my eventual booking.

here's what i did book, all on 4/15:
ORD-SJU-DFW-SFO. 5700 base miles, plus the 100% PLT bonus. total cost: $770, including taxes.

While Sameer's math is right, he neglected to calculate that since it's on the firm, the cents per mile works out to 0!

The ORD-SJU and SJU-DFW segments look very full in coach, so maybe I'll get lucky and get bumped.