Nagog Hill is 3 parts, but yes, it's hard, but now it seems normal to me. The way to deal with hills like that is to get in your lowest gear and spin up. Who cares how fast you go? Then, you can work on increasing your speed, if you want. I remember the first time I rode up Nashoba Rd., coming from Central St. I think my DH had to give me an assist, by pushing me with the back of his hand! But, it is mostly psychological once you know you have a certain amount of strength and endurance.
Your brother probably knows Scott. We also had an exchange student who went to AB for a semester, who is a cyclist (was a pro in Germany and now is in school in Colorado) who he might remember. Scott was just a normal (well... sort of) AB kid who did very well in HS, as well as being a top ranked junior level cyclist. If it wasn't for him, I wouldn't be riding. He's married and living in San Diego and is going to Afghanistan in October. Been to Iraq twice, as well as Spain and Cuba, and that little thing in Lebanon.
2015 Trek Silque SSL
Specialized Oura
2011 Guru Praemio
Specialized Oura
2017 Specialized Ariel Sport