For me it depends what the roll is for and if the consequences are clear, then we can have multiple rolls that make sense. For example, the first check is evading Netties attack with athletics. This makes sense. Then there is a persuasion check attached to make her rethink. That is still fine, however then there is the option of a third check, which is again a persuasion check on the same topic, which then makes only sense if you do not want the player to go that route. And then it is sort of bad game design, as multiple rolls will greatly decrease your chance of success, but a failure will just incentivize your more to just reload. Also while your bonuses are shown, the mali are not, so you can not make an educated guess about the real chances of passing the check.
It does not help that the consequences are not directly clear and neither are the other outcomes and solutions to the issue at hand, some more intriguing and rewarding as the two clear options (persuasion and attacking).
