I decided to join the ranks of bike commuters rather than keep sinking money into car repair and parking. I haven't ridden a bike for about 20 years, and I'm at a lost on how to choose a suitable bike. First some stats about myself. I'm 38, 6'1, 180lbs. My commute is 7 miles one way, all city roads (half bike paths). The last 2 miles on the way home is straight uphill for about 300 ft (great for the morning, hell in the evening). I estimate that I'll at most carry 10lbs of cargo with me (likely a lot less most days).

Rather than asking for bike recommendations, I'd like to get some advice on how to choose one. The problem is that as an total newbie, I have no idea what "feel good" is (or what feels good for a mile but sucks for 7). So what are specific things I should watch out for? I don't have a tight budget, and I rather spend a little bit more to get a reliable and enjoyable bike rather than getting the cheapest. At the same time, I don't want to spend more than I have to.

Now that I think about it, shopping for a bike is a lot like shopping for a car...