Finally, after months and months and months of rolling up to one or both of the fishing contests, only to have my ass handed to me after 15 frantic minutes of fishing, I emerge victorious!
Most contests, I would be somewhere in the 32 - 37 Tastyfish range when the winner was announced. One time I actually got all 40 and hearthed to Booty Bay, only to be a split second behind the winner that day. I tried turning off addons, playing with my graphics settings, and engaging in mental acrobatics much like learning how to fly (according to The Hitchhiker's Guide): "It's no good deliberately intending to miss the ground because you won't." You can't go into the contest thinking you'll win. In fact, you must approach it as an unimportant but necessary task and downplay the importance of winning.
For me, it seems the crucial strategy was showing up just barely on time, throwing on my trusty Fishing Hat just before reaching my usual starting point (south of Grom'gol), complaining to a friend about obnoxious pool-sharers and uncharacteristically flying north along the coast, and then proceeding to nerdrage every time my bobber landed just to the side of the actual pool. Finally, I realized that I had only a few fish left and enough pools around me to reach it without traveling too far. Waiting for fish #40, I was practically vibrating in my seat, muttering "come on, come on, come on." It was an Oily Blackmouth. Cue gnashing of teeth and rending of clothes! I cast again, sure that a winner would be announced while I waited for the splash.
Tastyfish!! I hearthed to Booty Bay, promptly ran into the wall, then managed to navigate outside and run/fly to the turn-in. I didn't realize that the rewards had changed (or perhaps I never paid close enough attention to them in the first place), but didn't want to lose any time reading the item descriptions. I got a blue item that apparently turns me into a fish, which ain't half bad! Even better, this was the last achievement I needed to finally be awarded the Salty title!
guildie: Salty Akabeko, coming to a restaurant near you
me: nuuuu D:
guildie: what does Akabeko mean anyway?
me: ...red cow...
guildie: bahaha perfect
I look forward to resetting my hearthstone. Booty Bay was good to me, but I can't be tied down! I look forward to leisurely working on the rest of my fishing endeavors, namely hooking the riding turtle (agghh! Turtles again!) and doing some cross-faction stealth-fishing!