I live in Maine. The extent of the hilliness varies depending on specifics, but it's mostly relatively flat, in my opinion. Still, I like the range of gearing on my three speeds. I feel like, given the limited number of speeds, it's good that 1 and 3 lean slightly to the extremes. For a little bit of context, I spent years riding a single speed bike, so that might have a little bit to do with my preference. I like to keep it in 2 for most things, so if I'm going up or down, it's usually because of something relatively exaggerated (a hill, in one direction or the other). It occurs to me upon explaining it that other people probably prefer more subtlety, but still, I wouldn't think my preference is all THAT unusual.

As for my Sears bike, I should clarify it's specifics. I do not by any means claim to be an expert, but according to most of what I've gathered, my bike is probably a rebadged Puch. I could be wrong, but I think that makes it distinct from the Columbia ones. Hell if I know what I'm talking about though... anyway: I'd be lying if I said the derailur on that bike were all that spectacular, but after a lot of tweaking, I've gotten them to a point of "working" (I've only had this thing about 3 days). And by that, I mean I've gotten them to work about as well as I've gotten the derailur on any old road bike to work. On a 10 speed, I'm more willing to put up with the inherent fussiness of such a set up, because the payoff is more worthwhile. On a 5 speed, however, I find myself craving the smooth functionality (and range!) of a 3 speed hub.

Please pardon my complete ignorance about virtually everything, I've been biking all my life, but I've never been very active in the culture, so in many regards, I'm still a newbie, but I'm trying to learn.