Flying standby skipping fare points
In order to get a reasonable fare SJC-BOS without a saturday night stay for a business trip ($520 instead of $2200), I routed myself through LAS (and ORD) one way, and through (ORD and) PHX the other. The LAS/ORD is fine -- I get a nice 11 hours at the blackjack table. On the return, BOS-ORD-PHX-SJC, I'd love to take the nonstop BOS-SJC that leaves about an hour before my flight and gets in about seven hours earlier. Do I have any chance at standing by for it without having to pay the fare difference? (Recall that the fare is broken at PHX to save big $.) Will the gate/Admirals Club agents notice the two connections and multiple fare bases on my (paper) ticket if I try? Would it help if I called the night before to ask?
The nonstop is looking almost completely empty, though it is six weeks out.
Thanks!