Another trick for the flip flops is to use the small "belt" cinch strap that comes with some kites and wrap it around your waist with the f.f.s threaded through the belt.
I have done that several times. Then when done, you can use the cinch strap to pack down your kite with (the strap's original purpose). I find socks much easier though, b/c my ffs have broken a few times.
I have probably ridden the trolley 100 times over the last 9 years.
3 times the driver would not let me on, claiming surf boards were against the rules. So.... keep in mind that it's possible you won't get a ride, but rare.
One way to attempt to counter-act that is to bring a 5 dollar bill to pay with and hand it to the driver, and say "I don't want change". Not sure if coincidence, or if it helps, but since doing this I have not been denied a ride.
I also always have 7 quarters, just in case the bribe isn't understood and they demand exact change (happened once... guy was idiot I guess)
Anyway, the trolley
most of the time is cool. Even so, these days I try to arrange cars at DW and UW spots and view the trolley as a good back up for guys that break down or for days that others can't go.