By your description I'd say you live just north of me. Have some good climbing here especially in the berkshires. Climbing and descending are my favorite parts of cycling! I'll tell you what I did when I started riding here. I would attack the hills a couple times a week and really push myself up them in a slightly higher gear than normal. The rest of the time I would spin up them and just try to stay seated the whole way without blowing up. Eventually I found the style that best fit me and my abilities and actually enjoy climbing now. So keep at it and don't stick to one style because you read somewhere it was the best.

And headwinds comparable to hills? Are you nuts?! Give me Mount Everest before you give me a 5mph breeze!