I am fairly generous with checks - giving them for crits, any sort of action that would earn normal glory and using them as fuel for thematic mini-games during a session; plus I will use trait and passion checks like compels in Fate and offer them to players who are willing to get their characters into trouble.
My houserule for checks, which is mine, is to resolve the check as soon as I give it and to only physically put a tick on the sheet if the check is successful - any ticks will automatically increase next winter phase. This was originally done to make winter phase a little quicker but I liked how it gave players extra opportunity to advance a trait if they focused on it in play.
Regards
Luke