Can you do it without getting caught? Sure. But it ain't worth it, effects only become interesting if you invest a lot.
But as Anaris hinted, don't expect to make a 100/100/100/core region revolt just by spending a few hundred gold. I've used this tool on Athol Margos probably a dozen times so far, and it only had interesting effects at one occasion where it was already in bad shape. On the other hand, it does increase sympathy to your realm considerably, which is quite interesting if you want to FTO or CTO it.
Do it if the region has a large army or horde in it, or if it's starving (and only after the starvation effects started, not before), but otherwise don't bother. Also, do it by having in mind that you'll get caught, so if you have two characters on an island, always do it with the same, preferably the one with the least odds of getting captured.
Hmm, thank you for your detailed reply and explanation. It sure helpful to make the enemy region revolt when their army busy TO it after it gone rogue. Make their TO time longer.
My curious mind presents me with more questions.
1) So if the region is rogue, do we got caught by rogue if luck not on our side?
2) How luck factor out or is there any factors in how game determine we got caught doing this?
I liked the idea of "How dare you flirt with my sister?"
