You can certainly get plenty of wind. Chinooks off the mountains. Warms up the area in the winter. The ridge is a dividing line between WX systems. Certainly, lots of weather spills over. That said, you can often have one air mass on one side that doesn't cross and a completely different mass on the other side. I think the amount of wind is probably similar. Since the divide is higher, it tends to be cooler. On the south side, the air masses tedn to be more frequent southwest, and south pacific type air masses. The north side tend to frequent air masses from the north and Gulf of Alaska. That said, often they merge or are the same. But sometime split at the divide. Up slope and down slope have a major effect on the weather as well. Hopefully that's not confusing, and a decent description. If you think about the terrain, and the effect it has on air masses, it makes sense.
If you could be farther south. You might look at Florence. Much cheaper realestate. Horse property is easily doable within a few miles of the airport. Nice climate, bit hot in the summer. Easy to Colorado Springs airport, difficult to DIA. Probably the best winery in the state. The Abby.
