If you feel the need to make a challenge out of engaging someone on horseback, for instance, then have them roll their riding against some difficulty that you think is representative (14 sounds good to me, having no idea how hard it really is). If they get a defeat, the mechanical result is the penalty to do anything further on horseback until another suitable opportunity becomes available to make another roll. If they get a victory, the penalty probably applies to the difficulty on the next roll with that horse - the character gets used to that mount. If/when he gets a complete success, then he's mastered doing things with that horse, and never needs to roll again for that sort of circumstance.
Mike
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