I have two steel cyclocross bikes that I use almost exclusively on the road. (Surly Cross Check, like so many folks here on TE; and a Waterford X-12) Both of my cyclocross bikes have slick tires, which really make a huge difference on the speed. I'm comfortable with steel because I like the way it absorbs the road buzz, and I am very comfortable knowing that the sturdy cyclocross frame can handle any weird things I might do on the bikes. I do occasionally ride on dirt, gravel, and grass, and maybe once in a while I accidentally ride over a curb or pothole or two... or three.
One of my previous bikes was a Kona Dew. The same frame as a Jake, just set up as a hybrid (according to my LBS). The aluminum does transmit road buzz, and it bothered me quite a bit on rides longer than about 50 miles. But, oh, I did loooooove that bike!
Ask your LBS if you can take the Jake out for an hour or so. The geometry is sweet, a very willing bike, it will do whatever you ask of it. Then try a steel bike with similar geometry (Jamis Aurora, Surly Cross Check, etc). Some folks feel the difference between aluminum and steel on long rides, and some don't.
Considering the needs you listed, I really don't think you can go wrong with a cyclocross bike. When you fall in love with one, buy it!
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