how to beat the system - women's guerilla technic, tip#1:
we (or better my wife) succeeded very often (UA only) - when travelling with Gisela. Always when UA confirms or makes available only one upgraded seat - they put me (1K) automatically on it - and Gisela (not even Premier in 99) is waitlisted.
The system doesn't help - but many UA-individuals may. Gisela will start "flirting" - starting at check-in, if this didn't help then at the RCC and later with the agent at the gate, finally even when taking my upgraded seat on board - always saying them how lucky she is travelling with me this time, and asking naif if the airline would really allow her to accept my offer and take my upgraded seat.
I only remember 2 flights out of more than 10 in the last two years that this didn't end with (sometimes even a free) second upgrade.
Thinking again, she always succeeded with male, sometimes failed when talking to females ...