The Grand Prize winner for last year's Machinima contest, and also the winner in the Drama/Romance category was Snacky's Journal, Episode 4. I can definitely see why it won. It has a great story, voice acting, editing -- it's just an all around, well done piece of movie fun.
You see, Snacky is coerced (bribed) to go on a blind double date with his friend, only to find out that things are far more complicated... and profitable. I love the settings in Gadgetzan and the Darkmoon Faire, which are particularly appropriate considering the date is crossfaction. There is also an explanation in there as to why Murlocs have cash on them (though where the money is kept is still a mystery).
I hope you enjoy it as much as The Spawn and I did. She's insisting on a replay. AFK.