Here's my situation. I am a 40-year old male who didn't ride a bike from age 22 or so until age 38. Two years ago, my wife bought me a department-store bike (Schwinn entry level) so that I could ride with my kids. I ride with them often, but also have gotten hooked on my own. Last spring/summer/fall, I was riding 3-4 times per week, usually 10-20 miles ride. I want something better than my Schwinn, which never seems to stay adjusted properly and doesn't like hills all that much.
My rides are very hilly, with regular inclines of 10 to 12%, and occasionally 15%. Conquering the hills is my favorite part of riding, so I'd like something that suits that purpose well.
My longest ride to date was 30 miles. I'd like to be able to take longer charity rides, such as the 40 some-odd miles circling Manhattan, or eventually the 150 miles from Manhattan to Atlantic City.
I don't know jack about maintaining a bike, so I'm inclined to buy from a LBS that can service the rig.
I have about $700 to spend, but I want that to cover a new helmet, pedals, shoes, etc. Thus, I'm trying to stay in the $500 to $600 range. I've looked at the Cannondale Quick 5/6, the Gary Fisher Wingra, and the Scott T4/T5 at my LBS. Are these good choices? Or should I be looking at something else?