Is it less windy in a valley than on a hill?
Scenario #1 is relatively, somewhat, kinda, but-not-really accurate for summer, scenario #2 more so for winter. If you live in or near mountains, you are familiar with cold evening winds that come ripping through canyons and valleys to settle in basins. In mountainous vineyards of Europe, vine layout is routinely adjusted to dissipate these winds. Even if there is NO (weather-induced) wind, thermal gradients can create winds of their own. 

Winters see less of these thermal gradients and in general winds will be limited to higher altitudes where they blow pretty consistently. In both of your scenarios, however, winds blow pretty consistently at higher elevations....which is why wind farms are typically found there.