If the Dr. Good fits you well, the other 2011 Kona Asphalt bikes should fit you similarly if not identically. They all have similar or identical geometries.

32mm tires are pretty good for what you describe. If you decide you want something a little wider, you should be able to go wider without much trouble. ETRTO tire size 622-35 or 622-37 with fenders, even wider without (assuming the clearances are similar to the 2010 bikes).

Factory installed hardware will require the same maintenance as aftermarket. A factory-installed rack is still just bolted on, aside from rare examples where it's part of the frame. Buying all-in-one packages will drive the price up or drive the quality of components down, or both.

Finally, consider some normally geared bikes, especially if you don't plan on riding much in foul weather.

I personally have a 2010 Dr. Dew that I love. I've upgraded it with fenders, a rear rack, a dynamo hub, and dyno-driven lights. It's plugging along like a champ, even in the upstate New York winter.