First advice would be not to read the "official policy" unless you plan on printing it out and are prepared to recite from it. Like most policies, it's interpretation lies in the hands of whomever is on the other side of the counter. Can really only speak from experience on your questions, having done this many times.

First, $25 fee is for whole trip.

Secondly, only two factors have gotten me out of paying the $25. First are just nice gate agents that don't charge you. Second, is if I can't be confirmed for the flight I want, I challenge them having to pay the $25. I'll pay it if they give me a confirmed seat on the flight I want...but I have a problem paying $25 to stand around playing the standby game all afternoon. This often wins the argument.

Status doesn't help much in this game. You may want to try in the lounge??