The only trouble there is unless you are in the Rockies/out west you won't find many 8% grade hills where you can spend an hour on them. Here in the eastern part of the US the hills aren't that long. I know of one climb in eastern VT(Mount Ascutney) it's a 12% grade hill that's 3.7 miles long with an extended 18% grade stretch. Yeah, you climb over 2,000 feet going up it. I've climbed it twice, both times have been around 40 minutes to climb it.

As I've seen personally, I think I've mentioned it here in the past week or so on this thread or on another thread, wind is only wind depending on how the road is laid out. In one part of the country a stiff headwind may set you back quite nicely due to both the location of the road and the surrounding vegetation. In another part of the country the stiff headwind may be barely noticeable due having surrounding ground acting as a windbreak and the vegetation also acting as a windbreak. It's all very location determinate as to what kind of an effect you are going to notice from a 15-20+mph wind. Here in the Midwest, where I am right now, a 15-20mph wind is a real big deal. In New Hampshire where I live a 15-20mph headwind isn't much of a problem at all. It all depends on the where the road is located topographically.