Originally Posted by dynaryder

I have the Crosstrail Expert and love it. It's a little heavy compared to the other bikes you're looking at. It's actually closer to a MTB than a street bike.

I'm not digging the Treks because of the alloy forks. They ride rough and bother my carpel tunnel,YMMV. Also,the Soho's single front ring will limit your gearing and make it harder to pull the weight of a trailer.

The Bad Boys are nice. The Ultra gives you a street bike and MTB in one by just swapping the wheels,but it's out of your price range. The regular Bad Boys are pretty much pure street bikes.

I'd add two bikes to your list;the Kona Dew Deluxe and REI's Novara Safari. The Dew would do everything you ask and leave you with money left over,the Safari would also fit your needs and comes with a rear rack,can take a front rack,and has a cool trekking handlbar.

A cross bike would work as long as you have the gearing to pull a trailer. The only one I can think of off the top of my head in your price range is the Bianchi Volpe.

That Marinoni rocks.

Wider tires have more rolling resistance,but give a more comfortable ride and do better off road. If you're going to ride on the street and do some trails,you'll do best with tires in the 32-38mm range for 700cc wheels,and 1.5-2.0" range for 26" wheels.