Maybe not possible for the whole route. But, especially on a bike... you can spend 20 minutes going uphill and 2 minutes back down (or so). So if your hill is in the middle, it sure seems like one is going uphill both ways.

Yep, I've gone to school on a hill. Out the door of my house, and headed up the hill. Then coming home, it was out the door of the school and uphill again. I never had to worry about getting cold in the mornings as the hill was good at warming me up. Yep, there was the zipping around the loop at the top of the hill, and that brief downhill, but those uphill rides were the memorable parts.

As far as the winds, it is not uncommon for the morning and afternoon winds to be in the opposite direction. The trick is to choose a location for one's home to take advantage of the natural wind patterns.