Tricksters are intimidating to write simply BECAUSE their schemes are so absolutely beyond that which the "normals" could even comprehend. Tricksters are famous for their almost supernatural ability to walk out of a technical loss with a net gain. If it isn't nigh-supernatural, your aspiring writer reasons, then it must not be a well-written trickster.
In other words, if I can write it, then the trickster isn't tricky enough. That's false, of course - you only need a little bit of confidence. Tricksters are unexpectedly good at what they do, but they aren't magical. That's why I've found it easier to write a villain trickster than a protagonist trickster. The audience expects the villain to lose. The villain is supposed to lose, and nobody really looks at it from his point of view anyways, and so if he does something clever or logical, it comes as a bit of a surprise. Tricksters are never card-carrying villains - they always have a reason for what they do. Whenever I'm writing a villainous trickster, I use the following method: every time my villain gains a piece of information, I like to ask myself "given what he wants, what he knows, and what he has, what is the most absolute logical thing for my villain to do now?"
Being a bit of a guile hero in real life, I can probably say with a certain amount of confidence that being a guile hero isn't about planning a complex plan and using the batman gambit whenever possible. It's about planning a relatively simple plan, and just having a series of contingency "plan b" things available on the off chance that something goes wrong.
And of course, that's why it's so much fun to pit tricksters against one another. In the absence of opposition, the trickster's plan will be: get water. And they will get water.
The enemy trickster, of course, would want the same water. Or something. So, our trickster tells the rival's crazy ex girlfriend where he is, and while the rival is distracted, steals the water glass...
only the rival saw the way our trickster was eyeing his glass, and filled it with hydrogen peroxide. the real glass of water is hidden in the kitchen, which he accidentally lets slip, and then things get more complicated from there.
Trickster versus trickster drives the plot through characterization, not events. Tricksters make events happen. It's best not to have a plot in mind when you pit two tricksters against one another, because they can and will ruin it. Think of this in turns: trickster 1 takes his turn - look at what he knows, what he has, and then think of the most logical choice, and a backup plan just in case. Then trickster 2 takes his turn. Based on the actions of trickster 1, he has some information to work with. Does that make sense?
Bizarrely enough, Sun Tzu's The Art of War is great for this sort of thing, being itself a how-to for guile heroes.