Oh look we can keep the riddles with this system idea...
Using a similar system with the riddles that we do now is also a possibility. I've been thinking about it the last few weeks to myself and have come up with this solution, as I know a lot of people like the riddle system!

Bob the Outcast posts a stealth, as normal, with at least three clues. Characters guess as to whether it is their character, as usual, with a guess per 10 characters within each herd, and Outcasts blocking themselves. If no one guesses the stealth within the proper time allotment, Bob gets the item, per usual, so long as his clues pass. But what if the stealth is guessed? This is where things differ from our traditional system.

Here is our sample stealth:

You are a bird
dressed in white,
the desert stretches
glimmers on silver.

The stealth is targeting Sue of the Dragon's Throat, who guesses the clues as follows:

You are a bird
- Pegasus +1
a damsel in white,
- Sue is white +1
the desert stretches
- Sue is from the Dragon's Throat +1
glimmers on silver.
- Sue has silver hooves. +1

Bob will have sent the clues for this riddle to the Official account when he set up the stealth, to make sure he doesn't alter any of his solutions to beat out Sue. The PM looks sort of like this, with +# signifying the number of clues in that line that need to be guessed. More than one clue can exist in a line, and the same type of clue can be used as a valid point more than once. There may be up to 15 clues in your riddle, but there must be at least 3.

You are a bird,
- Pegasus +1
a damsel in white,
- Gender and color reference +2
the desert stretches
- Location +1
glimmers on silver.
- Silver hooves +1

Sue guessed for a total Clue Point score of 4, while Bob's stealth actually has a Clue Point score of 5. This means Bob wins the stealth, so long as all 5 of his clues are valid.

Characters who steal a lot can be rewarded through this system by adding an additional Clue Point for a certain number of stealths (similar to the battle buff system).

I feel like this system offers a lot more than our current one, in that it allows players to target characters that otherwise could not be stolen from (because they block every stealth they see with generic clues *cough*me*cough* :P). It encourages the use of literary skill, and displays the deceptive/clever nature of our sneaks, and critical reading and thinking skills on behalf of the person being stolen from.