How can I blueprint a boardgame's mechanics?

Ideally, I could set the commentary on the goings on in such situation, used for such a simulation (like - puting a “This will be hillarious”, or “This would be fortuitous” notes on the cards, based on the scenario) so that I could determine how playing which character in which scenario impacts the difficulty.
The idea is to emulate and simulate the playing process using this, so that I could determine whether certain scenarios and circumstances have anything for the player to hope for and whether the difficulty is within the desired parameters.
The desired parameters would be so that with any character under any circumstances there is a good reason for the player to hope for the best and fear the worst. So that each scenario would offer, let’s say, a 5% chance for a very fortuitous and very bad outcome and a healthy dose of those in between that would take some effort and/or luck for a good outcome.

Graphically and technically - it would be optimal if this could be graphically achieved using filters that correspond to said icons, so that a statistics window would show just what the player’s experience would likely be.

The ultimate goal is to introduce a measure of balance and consistency in the players’ experience.