I also found the dough difficult to roll out after chilling. That said, a little time at room temperature worked wonders. I received many compliments on the cookies, and I would definitely make them again. I recommend rolling the dough out a little more thinly than the recipe suggests.
I just threw out the Hamantaschen dough - it was dry and crumbly. I followed the recipe exactly - I thought some time in the fridge would help, but alas…I am always exacting in my measurements - this recipe is missing a liquid/moisture ingredient, perhaps an additional egg or 1/4 cup more butter? A complete failure!